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Information on EC 2.4.1.85 - cyanohydrin beta-glucosyltransferase
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2.4.1.85 cyanohydrin beta-glucosyltransferaseIUBMB Comments
Acts on a wide range of substrates in vitro, including cyanohydrins, terpenoids, phenolics, hexanol derivatives and plant hormones, in a regiospecific manner . This enzyme is involved in the biosynthesis of the cyanogenic glucoside dhurrin in sorghum, along with EC 1.14.14.36, tyrosine N-monooxygenase and EC 1.14.14.37, 4-hydroxyphenylacetaldehyde oxime monooxygenase. This reaction prevents the disocciation and release of toxic hydrogen cyanide .
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Word Map
- 2.4.1.85
- sorghum
-
cyanogenic
- dhurrin
- bicolor
-
glucosylates
- cyp71e1
-
three-fold
-
bitterness
-
stereo-selectively
-
r-mandelonitrile
-
quantitative-pcr
- diglucoside
- testa
-
mill
- amygdalus
- kernels
- batsch
-
prunus
- prunasin
-
metabolons
-
compartmentalised
-
non-bitter
- dulcis
- rosaceae
- almond
-
erratum
-
hypervariable
-
regiospecificity
- geraniol
- udp-glucosyltransferase
- agriculture
- biotechnology
- synthesis
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
ugt85b1, udp-glucose:p-hydroxymandelonitrile-o-glucosyltransferase, mandelonitrile glucosyltransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
glucosyltransferase, uridine diphosphoglucose-p-hydroxymandelonitrile
-
-
-
-
UDP-glucose-p-hydroxymandelonitrile glucosyltransferase
-
-
-
-
UGT85B1
uridine diphosphoglucose-cyanohydrin glucosyltransferase
-
-
-
-
uridine diphosphoglucose-p-hydroxymandelonitrile glucosyltransferase
-
-
-
-
uridine diphosphoglucose:aldehyde cyanohydrin beta-glucosyltransferase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-alpha-D-glucose + (S)-4-hydroxymandelonitrile = UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hexosyl group transfer
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
UDP-D-glucose:(S)-4-hydroxymandelonitrile beta-D-glucosyltransferase
Acts on a wide range of substrates in vitro, including cyanohydrins, terpenoids, phenolics, hexanol derivatives and plant hormones, in a regiospecific manner [3]. This enzyme is involved in the biosynthesis of the cyanogenic glucoside dhurrin in sorghum, along with EC 1.14.14.36, tyrosine N-monooxygenase and EC 1.14.14.37, 4-hydroxyphenylacetaldehyde oxime monooxygenase. This reaction prevents the disocciation and release of toxic hydrogen cyanide [3].
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CAS REGISTRY NUMBER
COMMENTARY
55354-52-4
-
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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
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 + 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 + beta-citronellol
UDP + beta-citronellol beta-D-glucoside
-
-
-
-
?
UDP-glucose + cis-3-hexen-1-ol
UDP + cis-3-hexenyl-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 + trans-2-hexen-1-ol
UDP + trans-2-hexenyl-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 + 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
-
-
?
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
?
-
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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NATURAL SUBSTRATE
NATURAL 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
UDP-D-glucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
UDP-glucose + 4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
-
-
-
-
?
UDPglucose + (S)-4-hydroxymandelonitrile
UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside
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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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
4-hydroxybenzaldehyde
potent inhibitor, 1 mg/ml bovine serum albumin protects
4-hydroxymandelonitrile
possibly an inhibitor, 1 mg/ml bovine serum albumin protects
mandelonitrile
potent inhibitor, 1 mg/ml bovine serum albumin protects
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
activity is 3fold greater in bitter almonds than in non-bitter types
brenda
additional information
-
68% of enzyme activity in epidermal and 32% in mesophyllic tissue
brenda
-
71% of enzyme activity in epidermal and 29% in mesophyllic tissue
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
UGT85B1 is found mainly in the soluble stroma fraction
brenda
transient expression of a fluorescent fusion protein in Sorghum bicolor epidermal cells as monitored by confocal laser scanning microscopy shows that UGT85B1-YFP accumulates in the cytoplasm in the absence of CYP79A1 or CYP71E1
brenda
transient expression of a fluorescent fusion protein in Sorghum bicolor epidermal cells as monitored by confocal laser scanning microscopy shows that UGT85B1-YFP in the presence of CYP79A1 and CYP71E1 shifts towards the surface of the ER membrane in the periphery of biosynthetic active cells
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
plant tcd2 mutants deficient in the enzyme have reduced vigor, being dwarfed, with poor root development and low fertility. The mutant plants accumulate numerous dhurrin pathway-derived metabolites, some of which are similar to those observed in transgenic Arabidopsis thaliana expressing the CYP79A1 and CYP71E1 genes. The tcd2 mutant suffers from self-intoxication because Sorghum does not have a feedback mechanism to inhibit the initial steps of dhurrin biosynthesis when the glucosyltransferase activity required to complete the synthesis of dhurrin is lacking. Phenotype, detailed overview
metabolism
physiological function
enzyme UGT85B1 is essential for formation of dhurrin in sorghum with no co-expressed endogenous UDP-glucosyltransferases able to replace it. Presence of metabolites in the tcd2 mutant which are suggested to be derived from dhurrin via endogenous pathways for nitrogen recovery, indicating which enzymes may be involved in such pathways, metabolites identification by LC-MS
metabolism
glucosylation of R-mandelonitrile to prunasin which is a precursor of amygdalin
metabolism
-
UGT85B1 is an important step in product channelling because a rapid glucosylation of the labile p-hydroxymandelonitrile product of CYP71E1 is necessary to avoid its dissociation into p-hydroxybenzaldehyde and hydrogen cyanide
metabolism
dhurrin is a cyanogenic glucoside and its synthesis from the amino acid tyrosine is catalysed by two membrane-bound cytochrome P450 enzymes (CYP79A1 and CYP71E1) and a soluble glucosyltransferase (UGT85B1), and is dependent on electron transfer from a P450 oxidoreductase
metabolism
dhurrin is a cyanogenic glucoside and its synthesis from the amino acid tyrosine is catalysed by two membrane-bound cytochrome P450 enzymes (CYP79A1 and CYP71E1) and a soluble glucosyltransferase (UGT85B1), and is dependent on electron transfer from a P450 oxidoreductase. Dhurrin biosynthesis in Sorghum and the formation of products derived from the different intermediates as part of the detoxification processes or as putative turnover products identified in the tcd2 mutant, overview
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). 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)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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