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UDP-alpha-D-glucose + phenol
UDP + phenyl beta-D-glucopyranoside
-
very poor substrate
-
-
?
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
UDP-glucose + (R,S)-mandelonitrile
UDP + prunasin
-
-
-
ir
UDP-glucose + 1-hexanol
UDP + hexyl beta-D-glucoside
-
-
-
-
?
UDP-glucose + 2-hydroxy-2-methylbutyronitrile
UDP + ?
-
-
-
-
?
UDP-glucose + 2-hydroxy-3-methoxybenzyl alcohol
UDP + ?
-
-
-
-
?
UDP-glucose + 3-methyl-2-buten-1-ol
UDP + 3-methyl-2-butenyl-beta-D-glucoside
-
-
-
-
?
UDP-glucose + 3-methyl-3-buten-1-ol
UDP + 3-methyl-3-butenyl-beta-D-glucoside
-
-
-
-
?
UDP-glucose + 4-hydroxybenzaldehyde
UDP + 4-formylphenyl beta-D-glucopyranoside
-
poor substrate, mixture of 4-hydroxybenzaldehyde with NaCN: good substrate
-
-
?
UDP-glucose + 4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
-
-
-
?
UDP-glucose + acetone cyanohydrin
UDP + ?
-
-
-
-
?
UDP-glucose + alpha-terpinol
UDP + alpha-terpinyl-beta-D-glucoside
-
-
-
-
?
UDP-glucose + benzyl alcohol
UDP + benzyl beta-D-glucoside
-
-
-
?
UDP-glucose + beta-citronellol
UDP + beta-citronellol beta-D-glucoside
-
-
-
-
?
UDP-glucose + cis-3-hexen-1-ol
UDP + cis-3-hexenyl-beta-D-glucoside
-
-
-
-
?
UDP-glucose + farnesol
UDP + farnesyl beta-D-glucoside
-
-
-
-
?
UDP-glucose + geraniol
UDP + geranyl-beta-D-glucoside
-
-
-
-
?
UDP-glucose + linalool
UDP + linalool beta-D-glucoside
-
-
-
-
?
UDP-glucose + mandelonitrile
UDP + 2-(beta-D-glucopyranosyl)-2-phenylacetonitrile
-
-
-
-
?
UDP-glucose + mandelonitrile
UDP + mandelonitrile beta-D-glucoside
specific for UDP-glucose
-
-
?
UDP-glucose + nerol
UDP + nerol beta-D-glucoside
-
-
-
-
?
UDP-glucose + trans-2-hexen-1-ol
UDP + trans-2-hexenyl-beta-D-glucoside
-
-
-
-
?
UDP-glucose + vanillic acid
UDP + vanillic acid beta-D-glucoside
-
-
-
-
?
UDP-glucose + vanillin
UDP + vanillin beta-D-glucoside
-
-
-
-
?
UDPalpha-D-glucose + benzoic acid
UDP + 1-O-benzoyl-beta-D-glucose
at 4% of the rate with p-hydroxymandelonitrile
-
-
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
UDPglucose + (S)-mandelonitrile
UDP + (S)-mandelonitrile beta-D-glucoside
UDPglucose + 4-hydroxybenzoic acid
UDP + glucosyl-4-hydroxybenzoate
-
poor substrate
-
-
?
UDPglucose + 4-hydroxybenzyl alcohol
UDP + 4-hydroxybenzyl glucoside
-
at 36% the rate of 4-hydroxymandelonitrile
-
-
?
UDPglucose + benzyl alcohol
UDP + benzylglucoside
at 13% of the rate with p-hydroxymandelonitrile
-
-
?
UDPglucose + geraniol
UDP + geraniol glucoside
at 11% of the rate with p-hydroxymandelonitrile
-
?
UDPglucose + hydroquinone
UDP + hydroquinone glucoside
-
at 41% the rate of 4-hydroxymandelonitrile
-
-
?
additional information
?
-
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
i.e. dhurrin
-
?
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
-
i.e. dhurrin
-
?
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
the glucosylation stabilizes the labile cyanohydrin
i.e. dhurrin
-
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
-
identical with dhurrin
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
-
identical with dhurrin
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
C-terminal region encodes the UDPglucose binding domain
identical with dhurrin
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
stereospecific for the S-enantiomer
identical with dhurrin
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
stereospecific for the S-enantiomer
identical with dhurrin
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
involved in dhurrin biosynthesis
dhurrin is the cyanogenic glucoside characteristic of Sorghum species
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
endogenous substrate is p-hydroxymandelonitrile, final step in the biosynthesis of dhurrin, transformation of the labile cyanohydrin into a stable storage form
-
?
UDPglucose + (S)-mandelonitrile
UDP + (S)-mandelonitrile beta-D-glucoside
at 78% of the rate with p-hydroxymandelonitrile
-
-
?
UDPglucose + (S)-mandelonitrile
UDP + (S)-mandelonitrile beta-D-glucoside
-
as good as 4-hydroxymandelonitrile
-
-
?
additional information
?
-
-
final enzyme of dhurrin biosynthesis
-
-
?
additional information
?
-
UGT85B1 has a broad substrate specificity
-
-
?
additional information
?
-
-
UGT85B1 has a broad substrate specificity
-
-
?
additional information
additional information
-
-
reaction is specific for an aromatic group, but not for a p-hydroxy substituent on the aromatic group, no substrates: catechol, resorcinol, phloroglucinol, fructose, glucose, dhurrin, acetone cyanohydrin, acetaldehyde cyanohydrin, GDPglucose, TDPglucose, ADPglucose
no product: taxiphyllin
?
additional information
additional information
-
exclusively specific for the presence of a benzyl group in the substrate, no substrate: acetone cyanohydrin, hydroquinone, p-hydroxybenzaldehyde, gentisic acid, caffeic acid, 2-hydroxy cinnamic acid, resveratrol, salicylic acid, p-hydroxymandelic acid, quercetin, caynidin, biochanin A, naringenin, apigenin, indole acetic acid, tomatidine
-
-
?
additional information
additional information
-
-
exclusively specific for the presence of a benzyl group in the substrate, no substrate: acetone cyanohydrin, hydroquinone, p-hydroxybenzaldehyde, gentisic acid, caffeic acid, 2-hydroxy cinnamic acid, resveratrol, salicylic acid, p-hydroxymandelic acid, quercetin, caynidin, biochanin A, naringenin, apigenin, indole acetic acid, tomatidine
-
-
?
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UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
UDP-glucose + (R,S)-mandelonitrile
UDP + prunasin
-
-
-
ir
UDP-glucose + 4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
-
-
-
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
additional information
?
-
-
final enzyme of dhurrin biosynthesis
-
-
?
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
i.e. dhurrin
-
?
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
the glucosylation stabilizes the labile cyanohydrin
i.e. dhurrin
-
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
involved in dhurrin biosynthesis
dhurrin is the cyanogenic glucoside characteristic of Sorghum species
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
endogenous substrate is p-hydroxymandelonitrile, final step in the biosynthesis of dhurrin, transformation of the labile cyanohydrin into a stable storage form
-
?
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HMNGT_SORBI
492
0
52916
Swiss-Prot
Chloroplast (Reliability: 4)
A0A2P6S0U3_ROSCH
287
0
32513
TrEMBL
other Location (Reliability: 2)
A0A0B2RBM6_GLYSO
115
0
13043
TrEMBL
other Location (Reliability: 5)
A0A5B7BP32_DAVIN
439
0
48164
TrEMBL
other Location (Reliability: 2)
A0A0B2QH61_GLYSO
197
0
21844
TrEMBL
other Location (Reliability: 4)
A0A5B7BUE1_DAVIN
112
0
12484
TrEMBL
other Location (Reliability: 5)
A0A5B7A6P5_DAVIN
324
0
36946
TrEMBL
other Location (Reliability: 2)
A0A396IU06_MEDTR
450
0
51191
TrEMBL
other Location (Reliability: 4)
A0A396IW77_MEDTR
164
0
18217
TrEMBL
other Location (Reliability: 2)
A0A0B2SCM1_GLYSO
454
0
51084
TrEMBL
Mitochondrion (Reliability: 5)
A0A0B2Q7A1_GLYSO
423
0
47573
TrEMBL
Mitochondrion (Reliability: 2)
G7KED9_MEDTR
471
0
53649
TrEMBL
other Location (Reliability: 4)
A0A396IT56_MEDTR
74
0
8481
TrEMBL
other Location (Reliability: 5)
A0A2P6S0U6_ROSCH
208
2
23101
TrEMBL
other Location (Reliability: 4)
A0A5B7C8J3_DAVIN
116
0
12685
TrEMBL
Chloroplast (Reliability: 4)
A0A5B7C0X0_DAVIN
190
0
20551
TrEMBL
other Location (Reliability: 3)
A0A5B7ACT9_DAVIN
377
0
42466
TrEMBL
Mitochondrion (Reliability: 5)
A0A0B2R517_GLYSO
180
0
20455
TrEMBL
other Location (Reliability: 4)
A0A2G9H0G8_9LAMI
246
0
28172
TrEMBL
other Location (Reliability: 4)
A0A2P6RTB0_ROSCH
71
0
8120
TrEMBL
other Location (Reliability: 1)
A0A2P6RZR6_ROSCH
495
0
55500
TrEMBL
other Location (Reliability: 2)
A0A2P6S3Y8_ROSCH
453
0
50770
TrEMBL
other Location (Reliability: 5)
A0A0B2Q2X1_GLYSO
482
0
54640
TrEMBL
other Location (Reliability: 5)
G7KED6_MEDTR
450
0
51185
TrEMBL
other Location (Reliability: 3)
A0A0B2R356_GLYSO
141
0
15513
TrEMBL
other Location (Reliability: 4)
A0A2I0AMQ7_9ASPA
368
0
41179
TrEMBL
other Location (Reliability: 5)
A0A2I0A482_9ASPA
794
0
87002
TrEMBL
Secretory Pathway (Reliability: 2)
A0A5B7A576_DAVIN
145
0
16460
TrEMBL
Secretory Pathway (Reliability: 5)
A0A0B2Q263_GLYSO
459
0
51457
TrEMBL
Mitochondrion (Reliability: 5)
A0A0B2PHW3_GLYSO
169
0
18341
TrEMBL
other Location (Reliability: 4)
A0A2G9FYQ1_9LAMI
68
0
7552
TrEMBL
other Location (Reliability: 2)
A0A5B7C6W2_DAVIN
109
0
11414
TrEMBL
other Location (Reliability: 3)
A0A396J0X5_MEDTR
295
0
33904
TrEMBL
other Location (Reliability: 2)
A0A2P6PFJ1_ROSCH
178
0
20124
TrEMBL
Chloroplast (Reliability: 5)
A0A2P6Q9K2_ROSCH
292
0
32640
TrEMBL
other Location (Reliability: 1)
A0A2P6RTA9_ROSCH
281
0
31678
TrEMBL
other Location (Reliability: 5)
A0A0B2PHX3_GLYSO
260
0
28697
TrEMBL
other Location (Reliability: 5)
A0A2G9GGA1_9LAMI
410
0
46355
TrEMBL
other Location (Reliability: 4)
A0A396HGU6_MEDTR
276
0
31448
TrEMBL
other Location (Reliability: 3)
A0A0B2RD24_GLYSO
145
0
15546
TrEMBL
other Location (Reliability: 2)
A0A5B6ZVQ5_DAVIN
142
0
16181
TrEMBL
other Location (Reliability: 2)
A0A396ITR0_MEDTR
191
0
22113
TrEMBL
other Location (Reliability: 2)
85A19_PRUDU
483
0
53697
Swiss-Prot
-
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E410A
glucosylation of mandelonitrile is 225fold reduced compared to wild-type enzyme
R201A
glucosylation of mandelonitrile is 20fold reduced compared to wild-type enzyme
S391A
glucosylation of mandelonitrile is 185fold reduced compared to wild-type enzyme
additional information
transgenic Arabidopsis thaliana plants that produce dhurrin are obtained by co-expression of CYP79A1/CYP71E1-CFP (cyan fluorescent protein)/UGT85B1-YFP (yellow fluorescent protein) and of CYP79A1/CYP71E1/UGT85B1-YFP (yellow fluorescent protein)
additional information
-
transgenic Arabidopsis thaliana plants that produce dhurrin are obtained by co-expression of CYP79A1/CYP71E1-CFP (cyan fluorescent protein)/UGT85B1-YFP (yellow fluorescent protein) and of CYP79A1/CYP71E1/UGT85B1-YFP (yellow fluorescent protein)
additional information
construction of a knockout mutant by use of targeted induced local lesions in genomes (TILLING) to identify a line with a mutation resulting in a premature stop codon in the N-terminal region of UGT85B1. Plants homozygous for this mutation do not produce dhurrin and are designated tcd2 (totally cyanide deficient 2) mutants. Phenotype, detailed overview
additional information
-
construction of a knockout mutant by use of targeted induced local lesions in genomes (TILLING) to identify a line with a mutation resulting in a premature stop codon in the N-terminal region of UGT85B1. Plants homozygous for this mutation do not produce dhurrin and are designated tcd2 (totally cyanide deficient 2) mutants. Phenotype, detailed overview
additional information
engineering for introduction of the dhurrin biosynthesis pathway, starting with L-tyrosine and comprising the enzymes CYP79A1, CYP71E1, and UGT85B1 into Nicotiana tabacum. Integration of genes CYP79A1, CYP71E1, and UGT85B1 into a neutral site of the Nicotiana tabacum chloroplast genome and functional expression, overview. The enzymes convert endogenous tyrosine into dhurrin using electrons derived directly from the photosynthetic electron transport chain, without the need for the presence of an NADPH-dependent P450 oxidoreductase. The dhurrin produced in the engineered plants amounted to 0.1-0.2% of leaf dry weight compared to 6% in the origin Sorghum bicolor
additional information
-
engineering for introduction of the dhurrin biosynthesis pathway, starting with L-tyrosine and comprising the enzymes CYP79A1, CYP71E1, and UGT85B1 into Nicotiana tabacum. Integration of genes CYP79A1, CYP71E1, and UGT85B1 into a neutral site of the Nicotiana tabacum chloroplast genome and functional expression, overview. The enzymes convert endogenous tyrosine into dhurrin using electrons derived directly from the photosynthetic electron transport chain, without the need for the presence of an NADPH-dependent P450 oxidoreductase. The dhurrin produced in the engineered plants amounted to 0.1-0.2% of leaf dry weight compared to 6% in the origin Sorghum bicolor
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Kojima, M.; Poulton, J.E.; Thayer, S.S.; Conn, E.E.
Tissue distributions of dhurrin and of enzymes involved in its metabolism in leaves of Sorghum bicolor
Plant Physiol.
63
1022-1028
1979
Sorghum bicolor
brenda
Reay, P.F.; Conn, E.E.
The purification and properties of a uridine diphosphate glucose: aldehyde cyanohydrin beta-glucosyltransferase from sorghum seedlings
J. Biol. Chem.
249
5826-5830
1974
Sorghum bicolor
brenda
Surkin Wurtele, E.; Thayer, S.S.; Conn, E.E.
Subcellular localization of a UDP-glucose:aldehyde cyanohydrin beta-glucosyl transferase in epidermal plastids of Sorghum leaf blades
Plant Physiol.
70
1732-1737
1982
Sorghum bicolor
brenda
Jones, P.R.; Moller, B.L.; Hoj, P.B.
The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor. Isolation, cloning, heterologous expression, and substrate specificity
J. Biol. Chem.
274
35483-35491
1999
Sorghum bicolor (Q9SBL1), Sorghum bicolor
brenda
Hansen, K.S.; Kristensen, C.; Tattersall, D.B.; Jones, P.R.; Olsen, C.E.; Bak, S.; Moller, B.L.
The in vitro substrate regiospecificity of recombinant UGT85B1, the cyanohydrin glucosyltransferase from Sorghum bicolor
Phytochemistry
64
143-151
2003
Sorghum bicolor
brenda
Thorsoe, K.S.; Bak, S.; Olsen, C.E.; Imberty, A.; Breton, C.; Moller, B.L.
Determination of catalytic key amino acids and UDP sugar donor specificity of the cyanohydrin glycosyltransferase UGT85B1 from Sorghum bicolor. Molecular modeling substantiated by site-specific mutagenesis and biochemical analyses
Plant Physiol.
139
664-673
2005
Sorghum bicolor (Q9SBL1), Sorghum bicolor
brenda
Kristensen, C.; Morant, M.; Olsen, C.E.; Ekstrom, C.T.; Galbraith, D.W.; Moller, B.L.; Bak, S.
Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome
Proc. Natl. Acad. Sci. USA
102
1779-1784
2005
Sorghum bicolor
brenda
Nielsen, K.A.; Tattersall, D.B.; Jones, P.R.; Muller, B.L.
Metabolon formation in dhurrin biosynthesis
Phytochemistry
69
88-98
2008
Sorghum bicolor (Q9SBL1), Sorghum bicolor
brenda
Franks, T.; Yadollahi, A.; Wirthensohn, M.; Guerin, J.; Kaiser, B.; Sedgley, M.; Ford, C.
A seed coat cyanohydrin glucosyltransferase is associated with bitterness in almond (Prunus dulcis) kernels [Erratum: 2008, v. 35, no. 4, p. 346.]
Funct. Plant Biol.
35
236-246
2008
Prunus dulcis (B2XBQ5)
brenda
Jensen, K.; Osmani, S.A.; Hamann, T.; Naur, P.; Moller, B.L.
Homology modeling of the three membrane proteins of the dhurrin metabolon: catalytic sites, membrane surface association and protein-protein interactions
Phytochemistry
72
2113-2123
2011
Sorghum bicolor
brenda
Gnanasekaran, T.; Karcher, D.; Nielsen, A.Z.; Martens, H.J.; Ruf, S.; Kroop, X.; Olsen, C.E.; Motawie, M.S.; Pribil, M.; M?ller, B.L.; Bock, R.; Jensen, P.E.
Transfer of the cytochrome P450-dependent dhurrin pathway from Sorghum bicolor into Nicotiana tabacum chloroplasts for light-driven synthesis
J. Exp. Bot.
67
2495-2506
2016
Sorghum bicolor (Q9SBL1), Sorghum bicolor
brenda
Blomstedt, C.K.; O'Donnell, N.H.; Bjarnholt, N.; Neale, A.D.; Hamill, J.D.; Moeller, B.L.; Gleadow, R.M.
Metabolic consequences of knocking out UGT85B1, the gene encoding the glucosyltransferase required for synthesis of dhurrin in Sorghum bicolor (L. Moench)
Plant Cell Physiol.
57
373-386
2016
Sorghum bicolor (Q9SBL1), Sorghum bicolor
brenda