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(R)-4-hydroxymandelonitrile
cyanide + 4-hydroxybenzaldehyde
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
2-chlorobenzaldehyde + HCN
(R)-2-chloromandelonitrile
-
-
after 96 h, 100% yield, 21% enantiomeric excess
-
?
2-chlorobenzaldehyde + nitromethane
1-(2-chlorophenyl)-2-nitroethanol
-
34% yield after 2 h
-
?
2-heptanone + HCN
(R)-2-heptanone cyanohydrin
-
needs long reaction time (26 h), providing low enantiomeric exess (14%), which supports the fact that methyl ketones of long aliphatic chain are poor substrates
-
-
?
2-methoxybenzaldehyde + nitromethane
1-(2-methoxyphenyl)-2-nitroethanol
-
13% yield after 2 h
-
?
2-methylbenzaldehyde + nitromethane
1-(2-methylphenyl)-2-nitroethanol
-
12% yield after 2 h
-
?
3,4-dihydroxybenzaldehyde + HCN
(R)-3,4-dihydroxymandelonitrile
-
-
after 96 h, 100% yield, 99% enantiomeric excess
-
?
3-(2-naphthyl)benzaldehyde + nitromethane
(1R)-1-[3-(naphthalen-2-yl)phenyl]-2-nitroethanol
-
7% yield after 2 h
-
?
3-chlorobenzaldehyde + nitromethane
1-(3-chlorophenyl)-2-nitroethanol
-
17% yield after 2 h
-
?
3-methoxybenzaldehyde + nitromethane
1-(3-methoxyphenyl)-2-nitroethanol
-
17% yield after 2 h
-
?
3-methylbenzaldehyde + nitromethane
1-(3-methylphenyl)-2-nitroethanol
-
12% yield after 2 h
-
?
3-phenylpropionaldehyde + HCN
(R)-2-hydroxy-4-phenylbutyronitrile
-
-
after 96 h, 83% yield, 91% enantiomeric excess
-
?
4-bromobenzaldehyde + HCN
(R)-4-bromomandelonitrile
-
-
after 96 h, 100% yield, 99% enantiomeric excess
-
?
4-bromobenzaldehyde + nitromethane
1-(4-bromophenyl)-2-nitroethanol
-
20% yield after 2 h
-
?
4-chlorobenzaldehyde + nitromethane
1-(4-chlorophenyl)-2-nitroethanol
-
9% yield after 2 h
-
?
4-fluorobenzaldehyde + HCN
(R)-4-fluoromandelonitrile
-
-
after 96 h, 100% yield, 72% enantiomeric excess
-
?
4-fluorobenzaldehyde + nitromethane
1-(4-fluorophenyl)-2-nitroethanol
-
9% yield after 2 h
-
?
4-methoxybenzaldehyde + nitromethane
1-(4-methoxyphenyl)-2-nitroethanol
-
2% yield after 2 h
-
?
4-methylbenzaldehyde + nitromethane
1-(4-methylphenyl)-2-nitroethanol
-
11% yield after 2 h
-
?
4-nitrobenzaldehyde + HCN
(R)-4-nitromandelonitrile
-
-
after 96 h, 100% yield, 14% enantiomeric excess
-
?
acetyltrimethylsilane + acetone cyanohydrin
?
-
both acetyltrimethylsilane conversion and enantiomeric excess of the product are above 99%
-
-
?
benzaldehyde + HCN
(R)-mandelonitrile
-
-
after 96 h, 100% yield, 99% enantiomeric excess
-
?
benzaldehyde + nitromethane
(R)-2-nitro-1-phenylethanol
-
30% yield after 2 h
-
?
cyanide + (2E)-3-methylpent-2-enal
(2R,3E)-2-hydroxy-4-methylhex-3-enenitrile
-
-
-
-
?
cyanide + (2E)-hex-2-enal
(2R,3E)-2-hydroxyhept-3-enenitrile
-
-
-
-
?
cyanide + (2E)-hex-2-enal
(3E)-2-hydroxyhept-3-enenitrile
-
53% enantiomeric excess
-
?
cyanide + (2E,4E)-hexa-2,4-dienal
(2R,3E,5E)-2-hydroxyhepta-3,5-dienenitrile
-
-
-
-
?
cyanide + (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
(2S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde is converted to 47.1% (2S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 52.9% (2R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
?
cyanide + (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde
(2S)-hydroxy-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile + (2R)-hydroxy-[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde is converted to 34.2% (2S)-hydroxy[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile and 65.8% (2R)-hydroxy[(4S,5S)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
-
?
cyanide + (4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde
(2S)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4R,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde is converted to 48.2% (2S)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 51.8% (2R)-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
?
cyanide + (4S)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
(2S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4S)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde is converted to 66.4% (2S)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 33.6% (2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
?
cyanide + (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde
(2S)-hydroxy-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile + (2R)-hydroxy-[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde is converted to 52.6% (2S)-hydroxy[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile and 47.4% (2R)-hydroxy[(4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]ethanenitrile
-
?
cyanide + (4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde
(2S)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile + (2R)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate (4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carbaldehyde is converted to 49.3% (2S)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile and 50.7% (2R)-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl](hydroxy)ethanenitrile
-
?
cyanide + (benzyloxy)acetaldehyde
(2R)-3-(benzyloxy)-2-hydroxypropanenitrile + (2S)-3-(benzyloxy)-2-hydroxypropanenitrile
-
-
43.9% (2S)-3-(benzyloxy)-2-hydroxypropanenitrile and 53.1% (2S)-3-(benzyloxy)-2-hydroxypropanenitrile
-
?
cyanide + (R)-4-methylsulfanylbenzaldehyde
(R)-4-methylsulfanyl-mandelonitrile
-
-
-
-
?
cyanide + 1,4-dioxaspiro[4.5]decane-2-carbaldehyde
(S)-2-hydroxy-2-((R)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile + (R)-2-hydroxy-2-((R)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile + (S)-2-hydroxy-2-((S)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile + (R)-2-hydroxy-2-((S)-1,4-dioxaspiro[4.5]decan-2-yl)acetonitrile
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate 1,4-dioxaspiro[4.5]decane-2-carbaldehyde is converted to 21.8% (2S)-(2R)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile, 28.3% (2R)-(2R)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile, 30.3% (2S)-(2S)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile and 19.6% (2R)-(2S)-1,4-dioxaspiro[4.5]dec-2-yl(hydroxy)ethanenitrile
-
?
cyanide + 1-phenylethanone
(2R)-2-hydroxy-2-phenylpropanenitrile
cyanide + 1-phenylethanone
2-hydroxy-2-phenylpropanenitrile
-
-
-
?
cyanide + 2,2-dimethylpropanal
(2R)-2-hydroxy-3,3-dimethylbutanenitrile
-
activity is 33% of the activity with benzaldehyde
9% enentiomeric excess
-
?
cyanide + 2,3,4a,8a-tetrahydro-1,4-benzodioxine-6-carbaldehyde
(2R)-hydroxy(2,3,4a,8a-tetrahydro-1,4-benzodioxin-6-yl)acetonitrile
-
isoenzyme HNL5
-
-
?
cyanide + 2,4-dimethylbenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethylphenyl)acetonitrile
cyanide + 2-(benzyloxy)-3-phenylpropanal
(2S,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile + (2R,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile + (2S,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile + (2R,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile
-
-
26.9% (2S,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile, 23.4% (2R,3S)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile, 29.2% (2S,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile and 20.6% (2R,3R)-3-(benzyloxy)-2-hydroxy-4-phenylbutanenitrile
-
?
cyanide + 2-(benzyloxy)propanal
(2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile + (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile + (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile + (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile
-
-
45.4% (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile, 8.1% (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile, 33.3% (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile and 13.3% (2S,3S)-3-(benzyloxy)-2-hydroxybutanenitrile
-
?
cyanide + 2-(naphthalen-2-yl)propanal
(2S,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile + (2S,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile + (2R,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile + (2R,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile
-
-
30.4% (2S,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile, 24.0% (2S,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile, 20.0% (2R,3S)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile and 25.6% (2R,3R)-2-hydroxy-3-(naphthalen-2-yl)butanenitrile
-
?
cyanide + 2-bromobenzaldehyde
(2R)-(2-bromophenyl)(hydroxy)ethanenitrile
-
98% enantiomeric excess
-
?
cyanide + 2-chlorobenzaldehyde
(2R)-(2-chlorophenyl)(hydroxy)ethanenitrile
cyanide + 2-chlorobenzaldehyde
(2R)-2-(2-chlorophenyl)-2-hydroxyacetonitrile
-
-
-
?
cyanide + 2-chlorobenzaldehyde
(R)-2-chloromandelonitrile
cyanide + 2-fluorobenzaldehyde
(2R)-(2-fluorophenyl)(hydroxy)ethanenitrile
-
99% enantiomeric excess
-
?
cyanide + 2-iodobenzaldehyde
(2R)-(2-iodophenyl)(hydroxy)ethanenitrile
-
more than 95% enantiomeric excess
-
?
cyanide + 2-methoxy-3-phenylpropanal
(2S,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile + (2R,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile + (2S,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile + (2R,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile
-
-
43.1% (2S,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile, 8.4 (2R,3S)-2-hydroxy-3-methoxy-4-phenylbutanenitrile, 40.1% (2S,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile and 8.4% (2R,3R)-2-hydroxy-3-methoxy-4-phenylbutanenitrile
-
?
cyanide + 2-methoxybenzaldehyde
(R)-2-hydroxy-2-(2-methoxyphenyl)acetonitrile
-
-
-
-
?
cyanide + 2-methoxybenzaldehyde
(R)-2-methoxymandelonitrile
-
-
-
-
r
cyanide + 2-methylbenzaldehyde
(R)-2-hydroxy-2-(2-methylphenyl)acetonitrile
-
-
-
-
?
cyanide + 2-methylpropanal
(2R)-2-hydroxy-3-methylbutanenitrile
-
activity is 67% of the activity with benzaldehyde
13% enentiomeric excess
-
?
cyanide + 2-naphthaldehyde
(R)-2-hydroxy-2-(naphthalen-2-yl)acetonitrile
-
-
-
?
cyanide + 2-phenylpropanal
(2R,3S)-2-hydroxy-3-phenylbutanenitrile + (2S,3R)-2-hydroxy-3-phenylbutanenitrile + (2R,3R)-2-hydroxy-3-phenylbutanenitrile
-
-
3.0% (2S,3S)-2-hydroxy-3-phenylbutanenitrile, 51.8% (2R,3S)-2-hydroxy-3-phenylbutanenitrile, 27.6% (2S,3R)-2-hydroxy-3-phenylbutanenitrile and + 17.6% (2R,3R)-2-hydroxy-3-phenylbutanenitrile
-
?
cyanide + 2-thiophenecarboxaldehyde
?
-
-
-
?
cyanide + 3,4-dihydro-1H-isochromene-3-carbaldehyde
(S)-2-hydroxy-2-((S)-isochroman-3-yl)acetonitrile + (S)-2-hydroxy-2-((R)-isochroman-3-yl)acetonitrile + (R)-2-hydroxy-2-((S)-isochroman-3-yl)acetonitrile + (R)-2-hydroxy-2-((R)-isochroman-3-yl)acetonitrile
-
-
28.6% (2S)-(3S)-3,4-dihydro-1H-isochromen-3-yl(hydroxy)ethanenitrile, 21.5% (2R)-(3S)-3,4-dihydro-1H-isochromen-3-yl(hydroxy)ethanenitrile, 28.7% (2S)-(3R)-3,4-dihydro-1H-isochromen-3-yl(hydroxy)ethanenitrile and 21.1% (2R)-(3R)-3,4-dihydro-1H-isochromen-3-yl(hydroxy)ethanenitrile
-
?
cyanide + 3,4-dihydroxybenzaldehyde
(R)-3,4-dihydroxymandelonitrile
cyanide + 3-bromobenzaldehyde
(2R)-(3-bromophenyl)(hydroxy)ethanenitrile
-
95% enantiomeric excess
-
?
cyanide + 3-chlorobenzaldehyde
(2R)-(3-chlorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 3-chlorobenzaldehyde
(R)-3-chloromandelonitrile
-
-
-
-
r
cyanide + 3-fluorobenzaldehyde
(2R)-(3-fluorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 3-hydroxy-2,2-dimethylpropanal
(2R)-2,5-dihydroxy-3,3-dimethylpentanenitrile
-
i.e. hydroxypivaldehyde
best enantiomeric excess is obtained at pH 2.5
-
?
cyanide + 3-iodobenzaldehyde
(2R)-(3-iodophenyl)(hydroxy)ethanenitrile
-
93% enantiomeric excess
-
?
cyanide + 3-methoxy-3-phenylpropanal
(2S,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile + (2R,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile + (2S,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile + (2R,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile
-
-
6.5% (2S,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile, 45.2% (2R,4S)-2-hydroxy-4-methoxy-4-phenylbutanenitrile, 14.0% (2S,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile, 34.3% (2R,4R)-2-hydroxy-4-methoxy-4-phenylbutanenitrile
-
?
cyanide + 3-methoxybenzaldehyde
(2R)-(3-methoxyphenyl)(hydroxy)ethanenitrile
-
-
-
?
cyanide + 3-methoxybenzaldehyde
(R)-3-methoxymandelonitrile
-
-
-
-
r
cyanide + 3-methylbenzaldehyde
(2R)-(3-methylphenyl)(hydroxy)ethanenitrile
-
-
-
?
cyanide + 3-phenoxybenzaldehyde
(2R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
-
more than 95% enantiomeric excess
-
?
cyanide + 3-phenoxybenzaldehyde
(R)-2-hydroxy-2-(3-phenoxy-phenyl)-acetonitrile
-
synthesis of (R)-2-hydroxy-2-(3-phenoxyphenyl)-acetonitrile with 93% enantiomeric excess
-
-
?
cyanide + 3-phenoxybenzaldehyde
(R)-3-phenoxymandelonitrile
-
-
-
-
r
cyanide + 3-phenoxypropanal
(2R)-2-hydroxy-5-phenylpentanenitrile
-
-
74.3% (2R)-2-hydroxy-5-phenylpentanenitrile and 25.7% (2S)-2-hydroxy-5-phenylpentanenitrile
-
?
cyanide + 3-phenylprop-2-enal
(2R)-2-hydroxy-4-phenylbut-3-enenitrile
-
-
-
?
cyanide + 3-phenylpropanal
(2R)-2-hydroxy-4-phenylbutanenitrile
cyanide + 3-phenylpropanal
(R)-2-hydroxy-4-phenylbutyronitrile
-
isoenzyme HNL5
-
-
?
cyanide + 3-phenylpropionaldehyde
(R)-2-hydroxy-4-phenyl butyronitrile
cyanide + 3-tetrahydrothiophenone
(S)-3-hydroxytetrahydrothiophene-3-carbonitrile
-
the enzyme, that shows (R)-stereospecificity for its natural substrate shows S-stereselectivity with the heterocyclic ketone as substrate
-
-
?
cyanide + 4-biphenylcarboxaldehyde
?
-
-
-
?
cyanide + 4-bromoacetophenone
4-bromo-2-hydroxyphenylpropionitrile
-
(R)-cyanohydrin is formed with 5% yield and 99% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + 4-bromobenzaldehyde
(2R)-(4-bromophenyl)(hydroxy)ethanenitrile
cyanide + 4-bromobenzaldehyde
(R)-4-bromomandelonitrile
-
synthesis of (R)-4-bromomandelonitrile with a yield pf 100% and an enantiomeric excess value of 99%
-
-
?
cyanide + 4-chloroacetophenone
4-chloro-2-hydroxyphenylpropionitrile
-
(R)-cyanohydrin is formed with 11% yield and 95% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + 4-chlorobenzaldehyde
(2R)-(4-chlorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 4-fluoroacetophenone
4-fluoro-2-hydroxyphenylpropionitrile
-
(R)-cyanohydrin is formed with 20% yield and 84% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + 4-fluorobenzaldehyde
(2R)-(4-fluorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 4-fluorobenzaldehyde
(R)-4-fluoromandelonitrile
cyanide + 4-hydroxybenzaldehyde
(2R)-(4-hydroxyphenyl)(hydroxy)ethanenitrile
-
97% enantiomeric excess
-
?
cyanide + 4-hydroxybenzaldehyde
(R)-4-hydroxymandelonitrile
cyanide + 4-hydroxybutanal
(R)-2,5-dihydroxypentanenitrile
-
by varying the different reaction parameters it is possible to reduce the extension of the undesirable non-enzymatic competing reactions and optimize the optical purity of the cyanohydrin product. Best results are obtained at 15°C
-
-
?
cyanide + 4-iodoacetophenone
4-iodo-2-hydroxyphenylpropionitrile
-
(R)-cyanohydrin is formed with 3% yield and 24% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + 4-iodobenzaldehyde
(2R)-(4-iodophenyl)(hydroxy)ethanenitrile
-
92% enantiomeric excess
-
?
cyanide + 4-methoxybenzaldehyde
(2R)-(4-methoxyphenyl)(hydroxy)ethanenitrile
cyanide + 4-methoxybenzaldehyde
(2R)-hydroxy(4-methoxyphenyl)ethanenitrile
cyanide + 4-methoxybenzaldehyde
(R)-4-methoxymandelonitrile
-
-
-
-
r
cyanide + 4-methyl benzaldehyde
(2R)-(4-methylphenyl)(hydroxy)ethanenitrile
-
(R)-cyanohydrin is formed with 85% yield and 79% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + 4-methylbenzaldehyde
(2R)-(4-methylphenyl)(hydroxy)ethanenitrile
cyanide + 4-methylbenzaldehyde
(R)-4-methylmandelonitrile
-
-
-
-
r
cyanide + 4-nitrobenzaldehyde
(R)-4-nitromandelonitrile
-
synthesis of (R)-4-nitromandelonitrile with a yield of 100% and an enantiomeric excess value of 14%
-
-
?
cyanide + 4-phenylbutan-2-one
2-hydroxy-4-phenylbutyronitrile
-
-
-
-
?
cyanide + 4-phenylbutanal
(2R)-2-hydroxy-5-phenylpentanenitrile
-
-
88.9% (2R)-2-hydroxy-5-phenylpentanenitrile and 11.1% (2S)-2-hydroxy-5-phenylpentanenitrile
-
?
cyanide + 5-hydroxypentanal
(R)-2,6-dihydroxyhexanenitrile
-
by varying the different reaction parameters it is possible to reduce the extension of the undesirable non-enzymatic competing reaction and optimize the optical purity of the cyanohydrin product. Best results are obtained at 15°C
-
-
?
cyanide + 6-methylhept-5-en-2-one
(2R)-2-hydroxy-2,6-dimethylhept-5-enenitrile
-
-
-
?
cyanide + acetophenone
(2R)-hydroxyphenylpropionitrile
-
(R)-cyanohydrin is formed with 1% yield and 99% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
cyanide + butanal
(2R)-2-hydroxypentanenitrile
cyanide + cinnamaldehyde
(2R,3E)-2-hydroxy-4-phenylbut-3-enenitrile
-
i.e. (2E)-3-phenylprop-2-enal
-
-
?
cyanide + cyclohexanecarbaldehyde
(2R)-cyclohexyl(hydroxy)acetonitrile
-
activity is 41% of the activity with benzaldehyde
10% enentiomeric excess
-
?
cyanide + cyclohexanone
1-hydroxycyclohexanecarbonitrile
-
-
-
?
cyanide + decanal
(2R)-2-hydroxyundecanal
-
56% enantiomeric excess
-
?
cyanide + furan-2-carbaldehyde
(2R)-(furan-2-yl)(hydroxy)acetonitrile
-
isoenzyme HNL5
-
-
?
cyanide + furan-2-carbaldehyde
(2R)-furan-2-yl(hydroxy)ethanenitrile
cyanide + furan-2-carbaldehyde
(2S)-furan-2-yl-hydroxyacetonitrile
-
-
-
?
cyanide + hexan-2-one
(2R)-2-hydroxy-2-methylhexanenitrile
cyanide + hexanal
(2R)-2-hydroxyheptanenitrile
-
98% enantiomeric excess
-
?
cyanide + hydroxypivaldehyde
(R)-hydroxypivaldehyde cyanohydrin
-
crosslinked enzyme aggregates catalyze synthesis of (R)-hydroxypivaldehyde cyanohydrin under reaction conditions that immediately inactivated non-immobilized enzyme
-
-
r
cyanide + isobutyraldehyde
2-hydroxy-3-methylbutyronitrile
-
-
-
?
cyanide + naphthalen-2-ylacetaldehyde
(2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
-
-
3.5% (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile and 96.5% (2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
-
?
cyanide + naphthalen-2-ylacetaldehyde
(2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile + (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
-
-
33.2% (2R)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile and 66.8% (2S)-2-hydroxy-3-(naphthalen-2-yl)propanenitrile
-
?
cyanide + naphthalene-1-carbaldehyde
(2R)-hydroxy(naphthalen-1-yl)acetonitrile
-
isoenzyme HNL5
-
-
?
cyanide + naphthalene-2-carbaldehyde
(2R)-hydroxy(naphthalen-2-yl)acetonitrile
-
isoenzyme HNL5
-
-
?
cyanide + naphthalene-2-carbaldehyde
(2R)-hydroxy(naphthalen-2-yl)ethanenitrile
-
-
97.6% (2R)-hydroxy(naphthalen-2-yl)ethanenitrile and 2.4% (2S)-hydroxy(naphthalen-2-yl)ethanenitrile
-
?
cyanide + p-anisaldehyde
(R)-2-hydroxy-2-(4-methoxyphenyl)acetonitrile
-
-
-
?
cyanide + pentan-2-one
(2R)-2-hydroxy-2-methylpentanenitrile
cyanide + phenylacetaldehyde
(2R)-2-hydroxy-3-phenylpropanenitrile
cyanide + piperonal
(R)-2-hydroxy-2-(3,4-methylenedioxyphenyl)acetonitrile
-
-
-
?
cyanide + pivaldehyde
pivaloyl cyanide
-
-
-
?
cyanide + propanal
(2R)-2-hydroxybutanenitrile
-
activity is 20% of the activity with benzaldehyde
7% enentiomeric excess
-
?
cyanide + propionaldehyde
2-hydroxybutyronitrile
-
-
-
?
cyanide + pyridine-3-carbaldehyde
(2R)-hydroxy(pyridin-3-yl)acetonitrile
-
isoenzyme HNL5
-
-
?
cyanide + tetrahydro-2H-pyran-2-carbaldehyde
(2S)-hydroxy-[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile + (2R)-hydroxy-[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile + (2S)-hydroxy-[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile + (2R)-hydroxy-[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate tetrahydro-2H-pyran-2-carbaldehyde is converted to 47.6% (2S)-hydroxy[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile, 4.6% (2R)-hydroxy[(2R)-tetrahydro-2H-pyran-2-yl]ethanenitrile, 42.6% (2S)-hydroxy[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile and 5.2% (2R)-hydroxy[(2S)-tetrahydro-2H-pyran-2-yl]ethanenitrile
-
?
cyanide + tetrahydrofuran-2-carbaldehyde
(2S)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile + (2R)-hydroxy-[(2R)-tetrahydrofuran-2-yl]ethanenitrile + (2S)-hydroxy-[(2S)-tetrahydrofuran-2-yl]ethanenitrile + (2R)-hydroxy-[(2S)-tetrahydrofuran-2-yl]ethanenitrile
-
-
the natural substrate benzaldehyde is stereoselectively converted to (R)-mandelonitrile. The non-natural substrate tetrahydrofuran-2-carbaldehyde is converted to 33.7% (2S)-hydroxy[(2R)-tetrahydrofuran-2-yl]ethanenitrile, 16.2% (2R)-hydroxy[(2R)-tetrahydrofuran-2-yl]ethanenitrile, 35.6% (2S)-hydroxy[(2S)-tetrahydrofuran-2-yl]ethanenitrile and 14.5% (2R)-hydroxy[(2S)-tetrahydrofuran-2-yl]ethanenitrile
-
?
cyanide + thiophene-2-carbaldehyde
(2R)-hydroxy(thiophen-2-yl)acetonitrile
-
isoenzyme HNL5
-
-
?
cyanide + thiophene-2-carbaldehyde
(2R)-hydroxy(thiophen-2-yl)ethanenitrile
cyanide + thiophene-2-carbaldehyde
(2S)-hydroxy(thiophen-2-yl)ethanenitrile
-
activity is 2fold higher than with benzaldehyde
75% enentiomeric excess, The (S)-configuration is due to the Cahn-Ingold-Prelog rules
-
?
cyanide + thiophene-2-carbaldehyde
hydroxy(thiophen-2-yl)ethanenitrile
-
separation of enantiomers not posible
-
?
HCN + 1-naphthalenecarboxaldehyde
(R)-2-hydroxy-2-(1-naphthyl)acetonitrile
-
60% conversion
93% enantiomeric excess
-
?
HCN + 2,3,4,5-tetrafluorobenzaldehyde
(R)-2-hydroxy-2-(2,3,4,5-tetrafluorophenyl)acetonitrile
-
26% conversion
23% enantiomeric excess
-
?
HCN + 2,3,4-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3,4-trimethoxyphenyl)acetonitrile
-
14% conversion
% enantiomeric excess
-
?
HCN + 2,3,5,6-tetrafluorobenzaldehyde
(R)-2-hydroxy-2-(2,3,5,6-tetrafluorophenyl)acetonitrile
-
21% conversion
12% enantiomeric excess
-
?
HCN + 2,3,5-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3,5-trimethoxyphenyl)acetonitrile
-
16% conversion
28% enantiomeric excess
-
?
HCN + 2,3-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,3-dichlorophenyl)acetonitrile
-
11% conversion
22% enantiomeric excess
-
?
HCN + 2,3-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,3-dimethoxyphenyl)acetonitrile
-
7% conversion
37% enantiomeric excess
-
?
HCN + 2,4-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,4-dichlorophenyl)acetonitrile
-
13% conversion
78% enantiomeric excess
-
?
HCN + 2,4-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethoxyphenyl)acetonitrile
-
11% conversion
48% enantiomeric excess
-
?
HCN + 2,4-dimethylbenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethylphenyl)acetonitrile
-
5.8% conversion
86% enantiomeric excess
-
?
HCN + 2,5-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,5-dichlorophenyl)acetonitrile
-
8.8% conversion
57% enantiomeric excess
-
?
HCN + 2,5-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,5-dimethoxyphenyl)acetonitrile
-
9% conversion
63% enantiomeric excess
-
?
HCN + 2,6-dichlorobenzaldehyde
(R)-2-hydroxy-2-(2,6-dichlorophenyl)acetonitrile
-
10% conversion
12% enantiomeric excess
-
?
HCN + 2,6-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(2,6-dimethoxyphenyl)acetonitrile
-
6.5% conversion
32% enantiomeric excess
-
?
HCN + 2-allylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-allylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-allylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-allylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-allyloxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-allyloxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-allyloxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-allyloxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-butanone
(R)-2-hydroxy-2-methylbutyronitrile
-
48% conversion
72% enantiomeric excess
-
?
HCN + 2-chlorobenzaldehyde
(R)-2-hydroxy-2-(2-chlorophenyl)acetonitrile
HCN + 2-decanone
(R)-2-hydroxy-2-methyl-decanenitrile
-
18% conversion
52% enantiomeric excess
-
?
HCN + 2-ethoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-ethoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-ethoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-ethoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-ethylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-ethylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-ethylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-methylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-furancarboxaldehyde
(S)-2-hydroxy-2-(2-furyl)acetonitrile
-
1.2% conversion
98% enantiomeric excess
-
?
HCN + 2-heptanone
(R)-2-hydroxy-2-methyl-heptanenitrile
-
39% conversion
74% enantiomeric excess
-
?
HCN + 2-hexanone
(R)-2-hydroxy-2-methyl-hexanenitrile
-
48% conversion
80% enantiomeric excess
-
?
HCN + 2-methoxybenzaldehyde
(R)-2-hydroxy-2-(2-methoxyphenyl)acetonitrile
-
6.0% conversion
41% enantiomeric excess
-
?
HCN + 2-methoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-methoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-methoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-methoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-methylbenzaldehyde
(R)-2-hydroxy-2-(2-methylphenyl)acetonitrile
-
6% conversion
61% enantiomeric excess
-
?
HCN + 2-methylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-methylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-methylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-methylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-n-propoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-n-propoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-n-propoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-n-propoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-n-propylcyclohexanone
cis-(1R,2S)-1-hydroxy-2-n-propylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-n-propylcyclohexanone
trans-(1R,2R)-1-hydroxy-2-n-propylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 2-naphthalenecarboxaldehyde
(R)-2-hydroxy-2-(2-naphthyl)acetonitrile
-
58% conversion
98% enantiomeric excess
-
?
HCN + 2-nonanone
(R)-2-hydroxy-2-methyl-nonanenitrile
-
20% conversion
65% enantiomeric excess
-
?
HCN + 2-octanone
(R)-2-hydroxy-2-methyl-octanenitrile
-
22% conversion
67% enantiomeric excess
-
?
HCN + 2-pentanone
(R)-2-hydroxy-2-methyl-pentanenitrile
-
46% conversion
81% enantiomeric excess
-
?
HCN + 2-pyridinecarboxyaldehyde
(S)-2-hydroxy-2-(2-pyridyl)acetonitrile
-
89% conversion
22% enantiomeric excess
-
?
HCN + 2-quinolinecarboxaldehyde
(S)-2-hydroxy-2-(2-quinolinyl)acetonitrile
-
38% conversion
21% enantiomeric excess
-
?
HCN + 2-thiophenecarboxaldehyde
(S)-2-hydroxy-2-(2-thiophenyl)acetonitrile
-
31% conversion
88% enantiomeric excess
-
?
HCN + 2-trifluoromethylbenzaldehyde
(R)-2-hydroxy-2-(2-trifluoromethylphenyl)acetonitrile
-
72% conversion
5% enantiomeric excess
-
?
HCN + 2-undecanone
(R)-2-hydroxy-2-methyl-undecanenitrile
-
21% conversion
31% enantiomeric excess
-
?
HCN + 3,3-dimethyl-2-butanone
(R)-2-hydroxy-2,3,3-trimethyl-butyronitrile
-
28% conversion
38% enantiomeric excess
-
?
HCN + 3,4,5-trimethoxybenzaldehyde
(R)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)acetonitrile
-
24% conversion
31% enantiomeric excess
-
?
HCN + 3,4-dichlorobenzaldehyde
(R)-2-hydroxy-2-(3,4-dichlorophenyl)acetonitrile
-
7.9% conversion
94% enantiomeric excess
-
?
HCN + 3,4-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(3,4-dimethoxyphenyl)acetonitrile
-
13% conversion
78% enantiomeric excess
-
?
HCN + 3,5-dichlorobenzaldehyde
(R)-2-hydroxy-2-(3,5-dichlorophenyl)acetonitrile
-
21% conversion
92% enantiomeric excess
-
?
HCN + 3,5-dimethoxybenzaldehyde
(R)-2-hydroxy-2-(3,5-dimethoxyphenyl)acetonitrile
-
17% conversion
97% enantiomeric excess
-
?
HCN + 3-chlorobenzaldehyde
(R)-2-hydroxy-2-(3-chlorophenyl)acetonitrile
-
38% conversion
92% enantiomeric excess
-
?
HCN + 3-methoxybenzaldehyde
(R)-2-hydroxy-2-(3-methoxyphenyl)acetonitrile
-
31% conversion
92% enantiomeric excess
-
?
HCN + 3-methoxycyclohexanone
cis-(1R,3S)-1-hydroxy-3-methoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 3-methoxycyclohexanone
trans-(1R,3R)-1-hydroxy-3-methoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + 3-methyl-2-butanone
(R)-2-hydroxy-2,3-dimethyl-butyronitrile
-
39% conversion
42% enantiomeric excess
-
?
HCN + 3-methylbenzaldehyde
(R)-2-hydroxy-2-(3-methylphenyl)acetonitrile
-
7.5% conversion
87% enantiomeric excess
-
?
HCN + 3-methylcyclohexanone
cis-(1R,3S)-1-hydroxy-3-methylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 3-methylcyclohexanone
trans-(1R,3R)-1-hydroxy-3-methylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 3-nitrobenzaldehyde
(R)-2-hydroxy-2-(3-nitrophenyl)acetonitrile
-
87% conversion
65% enantiomeric excess
-
?
HCN + 3-phenoxybenzaldehyde
(R)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile
-
42% conversion
more than 99% enantiomeric excess
-
?
HCN + 3-pyridinecarboxyaldehyde
(R)-2-hydroxy-2-(3-pyridyl)acetonitrile
-
90% conversion
75% enantiomeric excess
-
?
HCN + 3-trifluoromethylbenzaldehyde
(R)-2-hydroxy-2-(3-trifluoro-methylphenyl)acetonitrile
-
91% conversion
68% enantiomeric excess
-
?
HCN + 3-trifluoromethylcyclohexanone
cis-(1R,3S)-1-hydroxy-3-trifluoromethylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 3-trifluoromethylcyclohexanone
trans-(1R,3R)-1-hydroxy-3-trifluoromethylcyclohexanecarbonitrile
-
-
-
-
?
HCN + 4-allyloxybenzaldehyde
(R)-2-hydroxy-2-(4-allyloxyphenyl)acetonitrile
-
6.4% conversion
98% enantiomeric excess
-
?
HCN + 4-benzyloxybenzaldehyde
(R)-2-hydroxy-2-(4-benzyloxyphenyl)acetonitrile
-
5.8% conversion
98% enantiomeric excess
-
?
HCN + 4-bromobenzaldehyde
(R)-2-hydroxy-2-(4-bromophenyl)acetonitrile
-
22% conversion
99% enantiomeric excess
-
?
HCN + 4-chlorbenzaldehyde
(R)-2-hydroxy-2-(4-chlorophenyl)acetonitrile
HCN + 4-fluorobenzaldehyde
(R)-2-hydroxy-2-(4-fluorophenyl)acetonitrile
-
28% conversion
% enantiomeric excess
-
?
HCN + 4-methoxybenzaldehyde
(R)-2-hydroxy-2-(4-methoxyphenyl)acetonitrile
-
17% conversion
97% enantiomeric excess
-
?
HCN + 4-methyl-2-pentanone
(R)-2-hydroxy-2,4-dimethyl-pentanenitrile
-
40% conversion
88% enantiomeric excess
-
?
HCN + 4-methylbenzaldehyde
(R)-2-hydroxy-2-(4-methylphenyl)acetonitrile
-
7.0% conversion
95% enantiomeric excess
-
?
HCN + 4-nitrobenzaldehyde
(R)-2-hydroxy-2-(4-nitrophenyl)acetonitrile
-
89% conversion
71% enantiomeric excess
-
?
HCN + 4-phenoxybenzaldehyde
(R)-2-hydroxy-2-(4-phenoxyphenyl)acetonitrile
-
-
-
?
HCN + 4-pyridinecarboxyaldehyde
(R)-2-hydroxy-2-(4-pyridyl)acetonitrile
-
65% conversion
41% enantiomeric excess
-
?
HCN + 4-quinolinecarboxaldehyde
(R)-2-hydroxy-2-(4-quinolinyl)acetonitrile
-
73% conversion
28% enantiomeric excess
-
?
HCN + 4-tert-butyldimethylsilyloxybenzaldehyde
(R)-2-hydroxy-2-(4-tert-butyldimethylsilyloxyphenyl)acetonitrile
-
4.8% conversion
97% enantiomeric excess
-
?
HCN + 4-trifluoromethylbenzaldehyde
(R)-2-hydroxy-2-(4-trifluoromethylphenyl)acetonitrile
-
90% conversion
76% enantiomeric excess
-
?
HCN + 5-methyl-2-hexanone
(R)-2-hydroxy-2,5-dimethyl-hexanenitrile
-
30% conversion
76% enantiomeric excess
-
?
HCN + acetophenone
2-hydroxyphenylpropionitrile
-
-
-
-
?
HCN + benzaldehyde
(R)-2-hydroxy-2-phenylacetonitrile
-
-
-
?
HCN + benzaldehyde
(R)-mandelonitrile
HCN + butanal
(R)-2-hydroxy-pentanenitrile
-
51% conversion
84% enantiomeric excess
-
?
HCN + cyclohexanecarboxaldehyde
(R)-2-hydroxy-2-cyclohexyl-acetonitrile
-
54% conversion
94% enantiomeric excess
-
?
HCN + cyclopentanecarboxaldehyde
(R)-2-hydroxy-2-cyclopentyl-acetonitrile
-
51% conversion
91% enantiomeric excess
-
?
HCN + decanal
(R)-2-hydroxyundecanenitrile
-
reaction in a two phase solvent system aqueous buffer and ionic liquid. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
-
-
?
HCN + dodecanal
(R)-2-hydroxytridecanenitrile
-
reaction in a two phase solvent system aqueous buffer and ionic liquid. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
-
-
?
HCN + hexanal
(R)-2-hydroxy-octanenitrile
-
38% conversion
81% enantiomeric excess
-
?
HCN + iso-propoxycyclohexanone
cis-(1S,2S)-1-hydroxy-2-iso-propoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + iso-propoxycyclohexanone
trans-(1S,2R)-1-hydroxy-2-iso-propoxycyclohexanecarbonitrile
-
-
-
-
?
HCN + isobutyraldehyde
(R)-2-hydroxy-3-methyl-butyronitrile
-
43% conversion
88% enantiomeric excess
-
?
HCN + pentanal
(R)-2-hydroxy-hexanenitrile
-
36% conversion
85% enantiomeric excess
-
?
HCN + piperonal
(R)-2-hydroxy-2-(3,4-methylenedioxyphenyl)acetonitrile
-
34% conversion
98% enantiomeric excess
-
?
HCN + pivaldehyde
(R)-2-hydroxy-3,3-dimethyl-butyronitrile
-
29% conversion
92% enantiomeric excess
-
?
HCN + propanal
(R)-2-hydroxy-butyronitrile
-
48% conversion
78% enantiomeric excess
-
?
HCN + trimethylsilylmethylketone
(R)-2-hydroxy-2-trimethylsilyl-propanenitrile
-
62% conversion
72% enantiomeric excess
-
?
HCN + undecanal
(R)-2-hydroxydodecanenitrile
-
reaction in a two phase solvent system aqueous buffer and ionic liquid. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
-
-
?
nitromethane + 2-chlorobenzaldehyde
(1R)-1-(2-chlorophenyl)-2-nitroethanol
-
34% yield, 68% enantiomeric excess
-
?
nitromethane + 3-methoxybenzaldehyde
(1R)-1-(3-methoxyphenyl)-2-nitroethanol
-
17% yield, 91% enantiomeric excess
-
?
nitromethane + 4-fluorobenzaldehyde
(1R)-1-(4-fluorophenyl)-2-nitroethanol
-
20% yield, 81% enantiomeric excess
-
?
nitromethane + benzaldehyde
(1R)-2-nitro-1-phenylethanol
30% yield, 91% enantiomeric excess
-
-
?
propiophenone + HCN
(S)-1-phenylacetone cyanohydrin
-
with 24% conversion and 46% enantiomeric exess
-
-
?
additional information
?
-
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
in a large number of plant species hydroxynitrile lyases catalyzes the decomposition of cyanohydrins in order to generate hydrogen cyanide upon tissue damage. Hydrogen cyanide serves as a deterrent against herbivores and fungi
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
-
modeling studies provide insights into the mechanism of cyanogenesis
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
Prunus pseudoarmeniaca
-
-
-
-
r
(R)-mandelonitrile
cyanide + benzaldehyde
in Prunus serotina Ehrh. macerates, the cyanogenic diglucoside (R)-amygdalin undergoes stepwise degradation to HCN catalyzed by amygdalin hydrolase, prunasin hydrolase, and (R)-(+)-mandelonitrile lyase
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
-
r
cyanide + 1-phenylethanone
(2R)-2-hydroxy-2-phenylpropanenitrile
-
-
-
-
r
cyanide + 1-phenylethanone
(2R)-2-hydroxy-2-phenylpropanenitrile
-
-
-
-
?
cyanide + 2,4-dimethylbenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethylphenyl)acetonitrile
-
-
-
?
cyanide + 2,4-dimethylbenzaldehyde
(R)-2-hydroxy-2-(2,4-dimethylphenyl)acetonitrile
-
-
-
-
?
cyanide + 2-chlorobenzaldehyde
(2R)-(2-chlorophenyl)(hydroxy)ethanenitrile
-
99% enantiomeric excess
-
?
cyanide + 2-chlorobenzaldehyde
(2R)-(2-chlorophenyl)(hydroxy)ethanenitrile
-
-
15.8% yield and 66% enantiomeric excess after 2 h
-
?
cyanide + 2-chlorobenzaldehyde
(R)-2-chloromandelonitrile
-
-
-
-
r
cyanide + 2-chlorobenzaldehyde
(R)-2-chloromandelonitrile
-
synthesis of (R)-2-chloromandelonitrile with a yield of 100% and an enantiomeric excess of 21%
-
-
?
cyanide + 2-chlorobenzaldehyde
(R)-2-chloromandelonitrile
-
-
-
-
?
cyanide + 2-chlorobenzaldehyde
(R)-2-chloromandelonitrile
-
-
-
-
r
cyanide + 3,4-dihydroxybenzaldehyde
(R)-3,4-dihydroxymandelonitrile
-
synthesis of (R)-3,4-dihydroxymandelonitrile with a yield of 100% and an enantiomeric excess of 99%
-
-
?
cyanide + 3,4-dihydroxybenzaldehyde
(R)-3,4-dihydroxymandelonitrile
-
-
-
-
?
cyanide + 3,4-dihydroxybenzaldehyde
(R)-3,4-dihydroxymandelonitrile
-
-
-
-
r
cyanide + 3-phenylpropanal
(2R)-2-hydroxy-4-phenylbutanenitrile
-
68% enantiomeric excess
-
?
cyanide + 3-phenylpropanal
(2R)-2-hydroxy-4-phenylbutanenitrile
-
-
-
?
cyanide + 3-phenylpropionaldehyde
(R)-2-hydroxy-4-phenyl butyronitrile
-
synthesis of (R)-2-hydroxy-4-phenyl butyronitrile with a yield of 83% and an enantiomeric excess of 91%
-
-
?
cyanide + 3-phenylpropionaldehyde
(R)-2-hydroxy-4-phenyl butyronitrile
-
-
-
-
r
cyanide + 4-bromobenzaldehyde
(2R)-(4-bromophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
cyanide + 4-bromobenzaldehyde
(2R)-(4-bromophenyl)(hydroxy)ethanenitrile
-
-
-
?
cyanide + 4-fluorobenzaldehyde
(R)-4-fluoromandelonitrile
-
-
-
-
r
cyanide + 4-fluorobenzaldehyde
(R)-4-fluoromandelonitrile
-
synthesis of (R)-4-fluoromandelonitrile with a yield of 100% and an enantiomeric excess value of 72%
-
-
?
cyanide + 4-hydroxybenzaldehyde
(R)-4-hydroxymandelonitrile
-
-
-
-
r
cyanide + 4-hydroxybenzaldehyde
(R)-4-hydroxymandelonitrile
-
(R)-cyanohydrin is formed with 2% yield and 25% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + 4-methoxybenzaldehyde
(2R)-(4-methoxyphenyl)(hydroxy)ethanenitrile
-
68% enantiomeric excess
-
?
cyanide + 4-methoxybenzaldehyde
(2R)-(4-methoxyphenyl)(hydroxy)ethanenitrile
-
-
-
?
cyanide + 4-methoxybenzaldehyde
(2R)-(4-methoxyphenyl)(hydroxy)ethanenitrile
-
-
-
-
?
cyanide + 4-methoxybenzaldehyde
(2R)-(4-methoxyphenyl)(hydroxy)ethanenitrile
-
(R)-cyanohydrin is formed with 95% yield and 95% enantiomeric excess, after 96 h at pH 4.0 and 5°C, cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase
-
-
r
cyanide + 4-methoxybenzaldehyde
(2R)-hydroxy(4-methoxyphenyl)ethanenitrile
-
-
-
-
r
cyanide + 4-methoxybenzaldehyde
(2R)-hydroxy(4-methoxyphenyl)ethanenitrile
-
-
-
-
?
cyanide + 4-methoxybenzaldehyde
(2R)-hydroxy(4-methoxyphenyl)ethanenitrile
-
-
-
-
?
cyanide + 4-methylbenzaldehyde
(2R)-(4-methylphenyl)(hydroxy)ethanenitrile
-
-
-
?
cyanide + 4-methylbenzaldehyde
(2R)-(4-methylphenyl)(hydroxy)ethanenitrile
-
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
more than 99% enantiomeric excess
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
the enzyme catalyzes the synthesis of (R)-mandelonitrile from benzaldehyde with a 99% enantiomeric excess
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
preference for (R)-product of 28%
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
90% enantiomeric excess at 80% conversion using 0.5 M benzaldehyde in a biphasic reaction system with methyl tertiary butyl ether
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
90% enantiomeric excess at 80% conversion using 0.5 M benzaldehyde in a biphasic reaction system with methyl tertiary butyl ether
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
several parameters influence the enantiomeric purity of the product and initial velocity of the reaction. Both pH and temperature are important parameters controlling the enantiomeric purity of the product. The optimum pH and temperature are pH 4 and 10°C, respectively. At the optimum pH and temperature, the spontaneous non-enzymatic reaction yielding the racemic mandelonitrile is almost completely suppressed. The initial velocity is markedly affected by the type of organic solvent in the biphasic system, while high enantiomeric purity is obtained when organic solvents having log P lower than 3.5 are used. The highest initial velocity of reaction and enantiomeric purity of (R)-mandelonitrile are obtained in the biphasic system of dibutyl ether with the aqueous phase content of 30% (v/v). The optimum substrate concentrations are 250 mM for benzaldehyde and 900 mM for acetone cyanohydrin, and the optimum enzyme concentration is 26.7 units/ml. The highest enantiomeric purity of (R)-mandelonitrile is successfully obtained with conversion and enantiomeric excess of 31.6% and 98.6%, respectively
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
the glycosylated enzyme efficiently performs transcyanation of (R)-mandelonitrile with a 98% enantiomeric excess in a biphasic system with diisopropyl ether
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
82% yield, 99% enantiomeric excess
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
more than 99% enantiomeric excess
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
synthesis of mandelonitrile is carried out with 89% molar conversion with 96% enantionmeric excess for R-mandelonitrile
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
the enzyme catalyses synthesis of (R)-mandelonitrile in methyl-tbutyl ether/citrate buffer biphasic system with more than 99% enantiomeric excess
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
90.3% yield and 100% enantiomeric excess after 2 h
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
99% yield, 99% enantiomeric excess
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
the formation of (R)-mandelonitrile from benzaldehyde and cyanide catalyzed by Prunus amygdalus hydroxynitrile lyase is chosen as a model reaction for the development and validation of a process model for production of (R)-cyanohydrins in an aqueous-organic biphasic-stirred tank reactor with an unknown interfacial area operated in batch mode. At 5°C and pH 5.5 the nonenzymatic reaction towards rac-mandelonitrile is largely suppressed
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
cross-linked enzyme aggregate of Prunus dulcis hydroxynitrile lyase achieve the synthesis of (R)-mandelonitrile, (R)-cyanohydrin is formed with 93% yield and 99% enantiopurity
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
synthesis of (R)-mandelonitrile with a yield of 100% and an enantiomeric excess of 99%
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
synthesis of (R)-mandelonitrile with 94% enantiomeric excess
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
more than 99% enantiomeric excess
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
Prunus pseudoarmeniaca
-
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
Prunus sp.
-
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
Prunus sp.
-
(R)-specific
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
-
more than 99% enantiomeric excess
-
?
cyanide + benzaldehyde
(R)-mandelonitrile
-
both pH and temperature have a large effect on the initial velocity and enantiomeric excess (e.e.) of the product, (R)-mandelonitrile. High enantiomeric purity of the product is observed at low pH and temperature because the non-enzymatic reaction producing racemates of mandelonitrile is almost suppressed. The optimum pH and temperature to obtain high enantiomeric excess are pH 4.0 and 10°C, respectively. The best solvent for the highest initial velocity and enantiomeric excess is diethyl ether with an optimum aqueous phase content of 50% (v/v). The initial reaction rate increases as the aqueous phase content rises, but when the content is more than 50%, a reduction of enantiomeric excess is observed. Increasing the concentration of the substrates accelerates the initial velocity, but causes a slight decrease in the e.e. of the product. Under the optimized conditions, the conversion and enantiomeric excess of (R)-mandelonitrile for 3 h are 40 and 99%, respectively
-
-
?
cyanide + butanal
(2R)-2-hydroxypentanenitrile
-
-
42% yield, 55% enantiomeric excess
-
?
cyanide + butanal
(2R)-2-hydroxypentanenitrile
-
100% yield, 90% enantiomeric excess
-
?
cyanide + furan-2-carbaldehyde
(2R)-furan-2-yl(hydroxy)ethanenitrile
-
-
-
-
r
cyanide + furan-2-carbaldehyde
(2R)-furan-2-yl(hydroxy)ethanenitrile
-
-
-
-
?
cyanide + furan-2-carbaldehyde
(2R)-furan-2-yl(hydroxy)ethanenitrile
-
-
-
-
?
cyanide + hexan-2-one
(2R)-2-hydroxy-2-methylhexanenitrile
-
95% enantiomeric excess
-
?
cyanide + hexan-2-one
(2R)-2-hydroxy-2-methylhexanenitrile
-
-
-
-
r
cyanide + hexan-2-one
(2R)-2-hydroxy-2-methylhexanenitrile
-
-
-
-
?
cyanide + hexan-2-one
(2R)-2-hydroxy-2-methylhexanenitrile
-
-
-
-
?
cyanide + pentan-2-one
(2R)-2-hydroxy-2-methylpentanenitrile
-
-
17% yield
-
?
cyanide + pentan-2-one
(2R)-2-hydroxy-2-methylpentanenitrile
-
-
-
?
cyanide + phenylacetaldehyde
(2R)-2-hydroxy-3-phenylpropanenitrile
-
96% enantiomeric excess
-
?
cyanide + phenylacetaldehyde
(2R)-2-hydroxy-3-phenylpropanenitrile
-
-
96.3% (2R)-2-hydroxy-3-phenylpropanenitrile and 3.7% (2S)-2-hydroxy-3-phenylpropanenitrile
-
?
cyanide + phenylacetaldehyde
(2R)-2-hydroxy-3-phenylpropanenitrile
-
isoenzyme HNL5
-
-
?
cyanide + thiophene-2-carbaldehyde
(2R)-hydroxy(thiophen-2-yl)ethanenitrile
-
-
87% yield, 99% enentiomeric excess
-
?
cyanide + thiophene-2-carbaldehyde
(2R)-hydroxy(thiophen-2-yl)ethanenitrile
-
48% yield, 87% enantiomeric excess
-
?
HCN + 2-chlorobenzaldehyde
(R)-2-hydroxy-2-(2-chlorophenyl)acetonitrile
-
-
-
?
HCN + 2-chlorobenzaldehyde
(R)-2-hydroxy-2-(2-chlorophenyl)acetonitrile
-
37% conversion
56% enantiomeric excess
-
?
HCN + 4-chlorbenzaldehyde
(R)-2-hydroxy-2-(4-chlorophenyl)acetonitrile
-
-
-
?
HCN + 4-chlorbenzaldehyde
(R)-2-hydroxy-2-(4-chlorophenyl)acetonitrile
-
21% conversion
99% enantiomeric excess
-
?
HCN + benzaldehyde
(R)-mandelonitrile
-
reaction in a two phase solvent system aqueous buffer and ionic liquid. When compared to the use of organic solvents as the nonaqueous phase, the reaction rate is significantly increased whereas the enantioselectivity remains good
-
-
?
HCN + benzaldehyde
(R)-mandelonitrile
-
13% conversion
93% enantiomeric excess
-
?
additional information
?
-
broad substrate range includes alphatic and aromatic aldehydes as well as ketones. Low activity with acetaldehyde, propionaldehyde and acetone cyanohydrin
-
-
?
additional information
?
-
-
broad substrate range includes alphatic and aromatic aldehydes as well as ketones. Low activity with acetaldehyde, propionaldehyde and acetone cyanohydrin
-
-
?
additional information
?
-
-
low activity towards acetone cyanohydrin
-
-
?
additional information
?
-
-
biocatalyst to synthesize a series of chiral methyl ketone cyanohydrins with satisfactory conversion and conspicuous enantiomeric excess. 2',6'-dimethylacetophenone, a compound with steric hindrance on the phenyl group is unsuitable as substrate
-
-
?
additional information
?
-
-
the enzyme activity toward 2-methylbenzaldehyde, 2,4-dimethylbenzaldehyde and 3-methoxybenzaldehyde is very low
-
-
?
additional information
?
-
-
activity is less than 5% of the activity with benzaldehyde: 4-methoxybenzaldehyde, naphthalene-1-carbaldehyde, naphthalene-2-carbaldehyde and 1,3-benzodioxole-5-carbaldehyde
-
-
?
additional information
?
-
-
aliphatic carbonyls are poorly converted
-
-
?
additional information
?
-
-
naphthyl and alkoxy substituents in the alpha- and also in the beta-position to the aldehyde group significantly influence the stereochemical outcome of the oxynitrilase-catalyzed transformation. No activity with methoxy(phenyl)acetaldehyde
-
-
?
additional information
?
-
-
substrates having ortho substituents are poor substrates in terms of enantioselectivity of the resulting cyanohydrins
-
-
?
additional information
?
-
-
the enzyme does not accept 3,3-dimethyl-2-butanone as substrate
-
-
?
additional information
?
-
-
synthesis of optically active (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide by asymmetric transcyanation of acetyltrimethylsilane with acetone cyanohydrin in a biphasic system. The substrate conversion and the product enantiomeric excess are 95% and 98% under the optimized conditions. Acetyltrimethylsilane was a better substrate of the enzyme than its carbon counterpart
-
-
?
additional information
?
-
-
the enzyme also catalyzes transcyanation of benzaldehyde and acetone cyanohydrin to (R)-mandelonitrile
-
-
?
additional information
?
-
the enzyme is active towards aromatic and aliphatic aldehydes and shows a preference for small substrates over bulky one
-
-
?
additional information
?
-
-
the enzyme is active towards aromatic and aliphatic aldehydes and shows a preference for small substrates over bulky one
-
-
?
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Wajant, H.; Foerster, S.; Selmar, D.; Effenberger, F.; Pfizenmaier, K.
Purification and characterization of a novel (R)-mandelonitrile lyase from the fern Phlebodium aureum
Plant Physiol.
109
1231-1238
1995
Phlebodium aureum, Prunus dulcis (O24243)
brenda
Lauble, H.; Mueller, K.; Schindellin, H.; Foerster, S.; Effenberger, F.
Crystallization and preliminary X-ray diffraction studies of mandelonitrile lyase from almonds
Proteins Struct. Funct. Genet.
19
343-347
1994
Prunus dulcis
brenda
Zheng, L.; Poulton, J.E.
Temporal and spatial expression of amygdalin hydrolase and (R)-(+)-mandelonitrile lyase in black cherry seeds
Plant Physiol.
109
31-39
1995
Prunus serotina (P52706), Prunus serotina
brenda
Effenberger, F.; Foerster, S.; Wajant, H.
Hydroxynitrile lyases in stereoselective catalysis
Curr. Opin. Biotechnol.
11
532-539
2000
Prunus sp.
brenda
Willeman, W.F.; Hanefeld, U.; Straathof, A.J.J.; Heijnen, J.J.
Estimation of kinetic parameters by progress curve analysis for the synthesis of (R)-mandelonitrile by Prunus amygdalus hydroxynitrile lyase
Enzyme Microb. Technol.
27
423-433
2000
Prunus dulcis
brenda
de Gonzalo, G.; Brieva, R.; Gotor, V.
(R)-Oxynitrilase-catalyzed transformation of omega-hydroxyalkanals
J. Mol. Catal. B
19-20
223-230
2002
Prunus dulcis
-
brenda
Dreveny, I.; Kratky, C.; Gruber, K.
The active site of hydroxynitrile lyase from Prunus amygdalus: modeling studies provide new insights into the mechanism of cyanogenesis
Protein Sci.
11
292-300
2002
Prunus dulcis
brenda
Dreveny, I.; Gruber, K.; Glieder, A.; Thompson, A.; Kratky, C.
The hydroxynitrile L-lyase from almond: A lyase that looks like an oxidoreductase
Structure
9
803-815
2001
Prunus dulcis (O24243), Prunus dulcis
brenda
Lin, G.; Han, S.; Li, Z.
Enzymic synthesis of (R)-cyanohydrins by three (R)-oxynitrilase sources in micro-aqueous organic medium
Tetrahedron
55
3531-3540
1999
Rhaphiolepis bibas, Prunus armeniaca, Prunus persica
-
brenda
Bianchi, P.; Roda, G.; Riva, S.; Danieli, B.; Zabelinskaja-Mackova, A.; Griengl, H.
On the selectivity of oxynitrilases towards alpha-oxygenated aldehydes
Tetrahedron
57
2213-2220
2001
Prunus dulcis
-
brenda
Huang, S.R.; Liu, S.L.; Zong, M.H.; Xu, R.
Synthesis of (R)-2-trimethylsilyl-2-hydroxyl-ethylcyanide catalyzed with (R)-oxynitrilase from loquat seed meal
Biotechnol. Lett.
27
79-82
2005
Rhaphiolepis bibas
brenda
Weis, R.; Poechlauer, P.; Bona, R.; Skranc, W.; Luiten, R.; Wubbolts, M.; Schwab, H.; Glieder, A.
Biocatalytic conversion of unnatural substrates by recombinant almond R-HNL isoenzyme 5
J. Mol. Catal. B
29
211-218
2004
Prunus dulcis
-
brenda
van Langen, L.M.; Selassa, R.P.; van Rantwijk, F.; Sheldon, R.A.
Cross-linked aggregates of (R)-oxynitrilase: a stable, recyclable biocatalyst for enantioselective hydrocyanation
Org. Lett.
7
327-329
2005
Prunus dulcis
brenda
Gaisberger, R.P.; Fechter, M.H.; Griengl, H.
The first hydroxynitrile lyase catalysed cyanohydrin formation in ionic liquids
Tetrahedron
15
2959-2963
2004
Prunus dulcis
-
brenda
Kobler, C.; Bohrer, A.; Effenberger, F.
Hydroxynitrile lyase-catalyzed addition of HCN to 2- and 3-substituted cyclohexanones
Tetrahedron
60
10397-10410
2004
Prunus dulcis
-
brenda
Solis, A.; Luna, H.; Manjarrez, N.; Perez, H.I.
Study on the (R)-oxynitrilase activity of Pouteria sapota
Tetrahedron
60
10427-10431
2004
Pouteria sapota
-
brenda
Nanda, S.; Kato, Y.; Asano, Y.
A new (R)-hydroxynitrile lyase from Prunus mume: asymmetric synthesis of cyanohydrins
Tetrahedron
61
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Prunus mume
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Ueatrongchit, T.; Kayo, A.; Komeda, H.; Asano, Y.; H-Kittikun, A.
Purification and characterization of a novel (R)-hydroxynitrile lyase from Eriobotrya japonica (Loquat)
Biosci. Biotechnol. Biochem.
72
1513-1522
2008
Rhaphiolepis bibas (B7VF77), Rhaphiolepis bibas
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Liu, Z.; Pscheidt, B.; Avi, M.; Gaisberger, R.; Hartner, F.S.; Schuster, C.; Skranc, W.; Gruber, K.; Glieder, A.
Laboratory evolved biocatalysts for stereoselective syntheses of substituted benzaldehyde cyanohydrins
Chembiochem
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2008
Prunus dulcis
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Pscheidt, B.; Avi, M.; Gaisberger, R.; Hartner, F.S.; Skranc, W.; Glieder, A.
Screening hydroxynitrile lyases for (R)-pantolactone synthesis
J. Mol. Catal. B
52-53
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2008
Prunus dulcis
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Fang, F.; Ji, A.; Meng, Z.
Biosynthesis of chiral methyl ketone cyanohydrins catalyzed by oxynitrilase in Chaenomeles speciosa seed meal
React. Kinet. Catal. Lett.
93
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2008
Chaenomeles speciosa
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brenda
Andexer, J.; von Langermann, J.; Mell, A.; Bocola, M.; Kragl, U.; Eggert, T.; Pohl, M.
An R-selective hydroxynitrile lyase from Arabidopsis thaliana with an alpha/beta-hydrolase fold
Angew. Chem. Int. Ed. Engl.
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2007
Arabidopsis thaliana (Q9LFT6), Arabidopsis thaliana
brenda
Dreveny, I.; Andryushkova, A.S.; Glieder, A.; Gruber, K.; Kratky, C.
Substrate binding in the FAD-dependent hydroxynitrile lyase from almond provides insight into the mechanism of cyanohydrin formation and explains the absence of dehydrogenation activity
Biochemistry
48
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2009
Prunus dulcis (O24243)
brenda
Willeman, W.F.; Gerrits, P.J.; Hanefeld, U.; Brussee, J.; Straathof, A.J.; van der Gen, A.; Heijnen, J.J.
Development of a process model to describe the synthesis of (R)-mandelonitrile by Prunus amygdalus hydroxynitrile lyase in an aqueous-organic biphasic reactor
Biotechnol. Bioeng.
77
239-247
2002
Prunus dulcis (O24243)
brenda
Fechter, M.H.; Gruber, K.; Avi, M.; Skranc, W.; Schuster, C.; Pchlauer, P.; Klepp, K.O.; Griengl, H.
Stereoselective biocatalytic synthesis of (S)-2-hydroxy-2-methylbutyric acid via substrate engineering by using "thio-disguised" precursors and oxynitrilase catalysis
Chemistry
13
3369-3376
2007
Prunus dulcis
brenda
Ueatrongchit, T.; Tamura, K.; Ohmiya, T.; H-Kittikun, A.; Asano, Y.
Hydroxynitrile lyase from Passiflora edulis. Purification, characteristics and application in asymmetric synthesis of (R)-mandelonitrile
Enzyme Microb. Technol.
46
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2010
Passiflora edulis
brenda
Guterl, J.K.
Andexer, J.N.; Sehl, T.; von Langermann, J.; Frindi-Wosch, I.; Rosenkranz, T.; Fitter, J.; Gruber, K.; Kragl, U.; Eggert, T.; Pohl, M.: Uneven twins: comparison of two enantiocomplementary hydroxynitrile lyases with alpha/beta-hydrolase fold
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2009
Arabidopsis thaliana
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Ueatrongchit, T.; Komeda, H.; Asano, Y.; H-Kittikun, A.
Parameters influencing asymmetric synthesis of (R)-mandelonitrile by a novel (R)-hydroxynitrile lyase from Eriobotrya japonica
J. Mol. Catal. B
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2009
Rhaphiolepis bibas
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brenda
Suelves, M.; Puigdomenech, P.
Molecular cloning of the cDNA coding for the (R)-(+)-mandelonitrile lyase of Prunus amygdalus: temporal and spatial expression patterns in flowers and mature seeds
Planta
206
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1998
Prunus dulcis (O24243), Prunus dulcis
brenda
Roda, G.; Riva, S.; Danieli, B.
Almond oxynitrilase-catalyzed transformation of aldehydes is strongly influenced by naphthyl and alkoxy substituents
Tetrahedron
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3939-3949
1999
Prunus dulcis
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brenda
Fukuta, Y.; Nanda, S.; Kato, Y.; Yurimoto, H.; Sakai, Y.; Komeda, H.; Asano, Y.
Characterization of a new (R)-hydroxynitrile lyase from the Japanese apricot Prunus mume and cDNA cloning and secretory expression of one of the isozymes in Pichia pastoris
Biosci. Biotechnol. Biochem.
75
214-220
2011
Prunus mume, Prunus mume (B9X0I1), Prunus mume (B9X0I2)
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Fuhshuku, K.; Asano, Y.
Synthesis of (R)-beta-nitro alcohols catalyzed by R-selective hydroxynitrile lyase from Arabidopsis thaliana in the aqueous-organic biphasic system
J. Biotechnol.
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2011
Arabidopsis thaliana, Arabidopsis thaliana (Q9LFT6)
brenda
Tuekel, S.; Yildirim, D.; Alagoez, D.; Alptekin, O.; Yuecebilgi, G.; Bilgin, R.
Partial purification and immobilization of a new (R)-hydroxynitrile lyase from seeds of Prunus pseudoarmeniaca
J. Mol. Catal. B
66
161-165
2010
Prunus pseudoarmeniaca
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brenda
Liu, S.; Zong, M.
(R)-oxynitrilase from Prunus salicina catalysed synthesis of (R)-ketone-cyanohydrin by enantioselective transcyanation
Prog. Biochem. Biophys.
37
1212-1216
2010
Prunus salicina
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brenda
Hussain, Z.; Wiedner, R.; Steiner, K.; Hajek, T.; Avi, M.; Hecher, B.; Sessitsch, A.; Schwab, H.
Characterization of two bacterial hydroxynitrile lyases with high similarity to cupin superfamily proteins
Appl. Environ. Microbiol.
78
2053-2055
2012
endophytic bacterium Psm-BT4509 (G9DE15)
brenda
Scholz, K.E.; Kopka, B.; Wirtz, A.; Pohl, M.; Jaeger, K.E.; Krauss, U.
Fusion of a flavin-based fluorescent protein to hydroxynitrile lyase from Arabidopsis thaliana improves enzyme stability
Appl. Environ. Microbiol.
79
4727-4733
2013
Arabidopsis thaliana (Q9LFT6), Arabidopsis thaliana
brenda
Yildirim, D.; Tuekel, S.S.; Alagoez, D.
Crosslinked enzyme aggregates of hydroxynitrile lyase partially purified from Prunus dulcis seeds and its application for the synthesis of enantiopure cyanohydrins
Biotechnol. Prog.
30
818-827
2014
Prunus dulcis
brenda
Andexer, J.N.; Staunig, N.; Eggert, T.; Kratky, C.; Pohl, M.; Gruber, K.
Hydroxynitrile lyases with alpha/beta-hydrolase fold: two enzymes with almost identical 3D structures but opposite enantioselectivities and different reaction mechanisms
ChemBioChem
13
1932-1939
2012
Arabidopsis thaliana (Q9LFT6), Arabidopsis thaliana
brenda
Okrob, D.; Metzner, J.; Wiechert, W.; Gruber, K.; Pohl, M.
Tailoring a stabilized variant of hydroxynitrile lyase from Arabidopsis thaliana
ChemBioChem
13
797-802
2012
Arabidopsis thaliana (Q9LFT6), Arabidopsis thaliana
brenda
Hajnal, I.; Lyskowski, A.; Hanefeld, U.; Gruber, K.; Schwab, H.; Steiner, K.
Biochemical and structural characterization of a novel bacterial manganese-dependent hydroxynitrile lyase
FEBS J.
280
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2013
Granulicella tundricola (E8WYN5), Granulicella tundricola MP5ACTX9 (E8WYN5)
brenda
Alagz, D.; Tkel, S.; Yildirim, D.
Purification, immobilization and characterization of (R)-hydroxynitrile lyase from Prunus amygdalus turcomanica seeds and their applicability for synthesis of enantiopure cyanohydrins
J. Mol. Catal. B
101
40-46
2014
Prunus turcomanica
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Zheng, Y.; Xu, J.; Wang, H.; Lin, G.; Hong, R.; Yu, H.
Hydroxynitrile lyase isozymes from Prunus communis identification, characterization and synthetic applications
Adv. Synth. Catal.
359
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2017
Prunus dulcis
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brenda
Alagoez, D.; Tuekel, S.S.; Yildirim, D.
Enantioselective synthesis of various cyanohydrins using covalently immobilized preparations of hydroxynitrile lyase from Prunus dulcis
Appl. Biochem. Biotechnol.
177
1348-1363
2015
Prunus dulcis
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Isobe, K.; Kitagawa, A.; Kanamori, K.; Kashiwagi, N.; Matsui, D.; Yamaguchi, T.; Fuhshuku, K.I.; Semba, H.; Asano, Y.
Characterization of a novel hydroxynitrile lyase from Nandina domestica Thunb
Biosci. Biotechnol. Biochem.
82
1760-1769
2018
Nandina domestica
brenda
Kopka, B.; Diener, M.; Wirtz, A.; Pohl, M.; Jaeger, K.E.; Krauss, U.
Purification and simultaneous immobilization of Arabidopsis thaliana hydroxynitrile lyase using a family 2 carbohydrate-binding module
Biotechnol. J.
10
811-819
2015
Arabidopsis thaliana (Q9LFT6)
brenda
Yildirim, D.; Tkel, S.S.; Alagz, D.
Crosslinked enzyme aggregates of hydroxynitrile lyase partially purified from Prunus dulcis seeds and its application for the synthesis of enantiopure cyanohydrins
Biotechnol. Prog.
30
818-827
2014
Prunus dulcis
brenda
Asif, M.; Bhalla, T.C.
Hydroxynitrile lyase of wild apricot (Prunus armeniaca L.) purification, characterization and application in synthesis of enantiopure mandelonitrile
Catal. Lett.
146
1118-1127
2017
Prunus armeniaca
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brenda
Asif, M.; Bhalla, T.C.
Enantiopure synthesis of (R)-mandelonitrile Using Hydroxynitrile lyase of wild apricot (Prunus armeniaca L.) [ParsHNL] in aqueous/organic biphasic system
Catal. Lett.
147
1592-1597
2017
Prunus armeniaca
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brenda
Nuylert, A.; Ishida, Y.; Asano, Y.
Effect of glycosylation on the biocatalytic properties of hydroxynitrile lyase from the Passion Fruit, Passiflora edulis A comparison of natural and recombinant enzymes
ChemBioChem
18
257-265
2017
Passiflora edulis (A0A1L7NZN4)
brenda
Lanfranchi, E.; Grill, B.; Raghoebar, Z.; Van Pelt, S.; Sheldon, R.A.; Steiner, K.; Glieder, A.; Winkler, M.
Production of hydroxynitrile Lyase from Davallia tyermannii (DtHNL) in Komagataella phaffii and its immobilization as a CLEA to generate a robust biocatalyst
ChemBioChem
19
312-316
2018
Davallia tyermanii
brenda
Motojima, F.; Nuylert, A.; Asano, Y.
The crystal structure and catalytic mechanism of hydroxynitrile lyase from passion fruit, Passiflora edulis
FEBS J.
285
313-324
2018
Passiflora edulis (A0A1L7NZN4), Passiflora edulis
brenda
Yao, L.; Li, H.; Yang, J.; Li, C.; Shen, Y.
Purification and characterization of a hydroxynitrile lyase from Amygdalus pedunculata Pall
Int. J. Biol. Macromol.
118
189-194
2018
Prunus pedunculata
brenda
Pavkov-Keller, T.; Bakhuis, J.; Steinkellner, G.; Jolink, F.; Keijmel, E.; Birner-Gruenberger, R.; Gruber, K.
Structures of almond hydroxynitrile lyase isoenzyme 5 provide a rationale for the lack of oxidoreductase activity in flavin dependent HNLs
J. Biotechnol.
235
24-31
2016
Prunus dulcis (O24243), Prunus dulcis
brenda
Alagoz, D.; Tkel, S.; Yildirim, D.
Purification, immobilization and characterization of (R)-hydroxynitrile lyase from Prunus amygdalus turcomanica seeds and their applicability for synthesis of enantiopure cyanohydrins
J. Mol. Catal. B
101
40-46
2014
Prunus turcomanica
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brenda
Dadashipour, M.; Ishida, Y.; Yamamoto, K.; Asano, Y.
Discovery and molecular and biocatalytic properties of hydroxynitrile lyase from an invasive millipede, Chamberlinius hualienensis
Proc. Natl. Acad. Sci. USA
112
10605-10610
2015
Chamberlinius hualienensis (A0A0H5BR52)
brenda
Lanfranchi, E.; Pavkov-Keller, T.; Koehler, E.M.; Diepold, M.; Steiner, K.; Darnhofer, B.; Hartler, J.; Van Den Bergh, T.; Joosten, H.J.; Gruber-Khadjawi, M.; Thallinger, G.G.; Birner-Gruenberger, R.; Gruber, K.; Winkler, M.; Glieder, A.
Enzyme discovery beyond homology a unique hydroxynitrile lyase in the Bet v1 superfamily
Sci. Rep.
7
46738
2017
Davallia tyermanii (A0A1C9V3R0), Davallia tyermanii (A0A1C9V3R4), Davallia tyermanii (A0A1C9V3R6), Davallia tyermanii (A0A1C9V3S9)
brenda