4.1.2.10: (R)-mandelonitrile lyase
This is an abbreviated version!
For detailed information about (R)-mandelonitrile lyase, go to the full flat file.
Word Map on EC 4.1.2.10
-
4.1.2.10
-
cyanohydrin
-
prunus
-
synthesis
-
hcn
-
cherry
-
enantioselective
-
serotina
-
lyases
-
r-mandelonitrile
-
enantiomeric
-
amygdalus
-
diisopropyl
-
prunasin
-
cyanogenesis
-
hbhnl
-
hydrocyanic
-
hevea
-
s-selective
-
pharmacology
-
agriculture
- 4.1.2.10
- cyanohydrin
- prunus
- synthesis
- hcn
- cherry
-
enantioselective
- serotina
- lyases
-
r-mandelonitrile
-
enantiomeric
- amygdalus
-
diisopropyl
- prunasin
-
cyanogenesis
- hbhnl
-
hydrocyanic
-
hevea
-
s-selective
- pharmacology
- agriculture
Reaction
Synonyms
(R)-(+)-Mandelonitrile lyase, (R)-HNL, (R)-HNL5, (R)-hydroxynitrile lyase, (R)-Mandelonitrile lyase, (R)-Oxynitrilase, (R)-PeHNL, (R)-selective HNL, AciX9_0562, almond oxynitrilase, APHNL, AtHNL, cupin 2 conserved barrel domain protein, cupin 2 domain-containing protein, D-alpha-hydroxynitrile lyase, D-Hydroxynitrile lyase, D-Oxynitrilase, DtHNL1, EjHNL, FAD-HNL, HNL, HNL1, HNL2, HNL4, HNL5, Hydroxynitrile lyase, hydroynitrile lyase, Lyase, mandelonitrile, mandelonitrile lyase, MDL, Mdl1, NdHNL, Oxynitrilase, PaHNL, PaHNL1, PaHNL5, PaMDL, ParsHNL, PhaMDL, PmHNL, R-HNL, R-hydroxynitrile lyase, R-selective HNL, R-selective hydroxynitrile lyase
ECTree
4.1.2.10 (R)-mandelonitrile lyaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 4.1.2.10 - (R)-mandelonitrile lyase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
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
(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
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-(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-(2-chlorophenyl)-2-hydroxyacetonitrile
-
-
-
?
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-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 + 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-bromobenzaldehyde
(2R)-(3-bromophenyl)(hydroxy)ethanenitrile
-
95% enantiomeric excess
-
?
cyanide + 3-chlorobenzaldehyde
(2R)-(3-chlorophenyl)(hydroxy)ethanenitrile
-
more than 99% enantiomeric excess
-
?
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-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-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
(R)-2-hydroxy-4-phenylbutyronitrile
-
isoenzyme HNL5
-
-
?
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-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
(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-hydroxybenzaldehyde
(2R)-(4-hydroxyphenyl)(hydroxy)ethanenitrile
-
97% enantiomeric excess
-
?
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-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-nitrobenzaldehyde
(R)-4-nitromandelonitrile
-
synthesis of (R)-4-nitromandelonitrile with a yield of 100% and an enantiomeric excess value of 14%
-
-
?
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 + 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 + decanal
(2R)-2-hydroxyundecanal
-
56% enantiomeric excess
-
?
cyanide + furan-2-carbaldehyde
(2R)-(furan-2-yl)(hydroxy)acetonitrile
-
isoenzyme HNL5
-
-
?
cyanide + furan-2-carbaldehyde
(2S)-furan-2-yl-hydroxyacetonitrile
-
-
-
?
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 + 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 + piperonal
(R)-2-hydroxy-2-(3,4-methylenedioxyphenyl)acetonitrile
-
-
-
?
cyanide + propanal
(2R)-2-hydroxybutanenitrile
-
activity is 20% of the activity with benzaldehyde
7% enentiomeric excess
-
?
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
(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-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-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 + 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
-
-
?
(R)-mandelonitrile
cyanide + benzaldehyde
-
-
-
r
(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
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
-
-
?
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
-
synthesis of (R)-2-chloromandelonitrile with a yield of 100% and an enantiomeric excess of 21%
-
-
?
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%
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-
?
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
-
synthesis of (R)-4-fluoromandelonitrile with a yield of 100% and an enantiomeric excess value of 72%
-
-
?
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
-
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
-
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
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-
?
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
-
-
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
-
-
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
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-
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
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-
r
cyanide + benzaldehyde
(R)-mandelonitrile
-
synthesis of (R)-mandelonitrile with a yield of 100% and an enantiomeric excess of 99%
-
-
?
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
-
-
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
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-
?
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 + pentan-2-one
(2R)-2-hydroxy-2-methylpentanenitrile
-
-
17% yield
-
?
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
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-
?
additional information
?
-
-
the enzyme activity toward 2-methylbenzaldehyde, 2,4-dimethylbenzaldehyde and 3-methoxybenzaldehyde is very low
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-
?
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
?
-
-
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
-
-
?
