KEGG   ORTHOLOGY: K13030
Entry
K13030                      KO                                     

Name
UGT85B1
Definition
cyanohydrin beta-glucosyltransferase [EC:2.4.1.85]
Pathway
ko00460  Cyanoamino acid metabolism
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
Module
M00369  Cyanogenic glycoside biosynthesis, tyrosine => dhurrin
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09106 Metabolism of other amino acids
   00460 Cyanoamino acid metabolism
    K13030  UGT85B1; cyanohydrin beta-glucosyltransferase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   01003 Glycosyltransferases
    K13030  UGT85B1; cyanohydrin beta-glucosyltransferase
Enzymes [BR:ko01000]
 2. Transferases
  2.4  Glycosyltransferases
   2.4.1  Hexosyltransferases
    2.4.1.85  cyanohydrin beta-glucosyltransferase
     K13030  UGT85B1; cyanohydrin beta-glucosyltransferase
Glycosyltransferases [BR:ko01003]
 Others
  Hydrophobic molecule
   K13030  UGT85B1; cyanohydrin beta-glucosyltransferase
Other DBs
RN: R04296 R04948
GO: 0047792
CAZy: GT1
Genes
BDI: 100843904
ATS: 109786124(LOC109786124)
SBI: 8060874
ZMA: 100284975
Reference
  Authors
Jones PR, Moller BL, Hoj PB
  Title
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.
  Journal
J Biol Chem 274:35483-91 (1999)
DOI:10.1074/jbc.274.50.35483
  Sequence
[sbi:8060874]

KEGG   ENZYME: 2.4.1.85
Entry
EC 2.4.1.85                 Enzyme                                 

Name
cyanohydrin beta-glucosyltransferase;
uridine diphosphoglucose-p-hydroxymandelonitrile glucosyltransferase;
UDP-glucose-p-hydroxymandelonitrile glucosyltransferase;
uridine diphosphoglucose-cyanohydrin glucosyltransferase;
uridine diphosphoglucose:aldehyde cyanohydrin beta-glucosyltransferase;
UDP-glucose:(S)-4-hydroxymandelonitrile beta-D-glucosyltransferase;
UGT85B1;
UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase;
UDP-D-glucose:(S)-4-hydroxymandelonitrile beta-D-glucosyltransferase
Class
Transferases;
Glycosyltransferases;
Hexosyltransferases
Sysname
UDP-alpha-D-glucose:(S)-4-hydroxymandelonitrile beta-D-glucosyltransferase (configuration-inverting)
Reaction(IUBMB)
UDP-alpha-D-glucose + (S)-4-hydroxymandelonitrile = UDP + (S)-4-hydroxymandelonitrile beta-D-glucoside [RN:R04296]
Reaction(KEGG)
R04296;
(other) R04948
Substrate
UDP-alpha-D-glucose [CPD:C00029];
(S)-4-hydroxymandelonitrile [CPD:C03742]
Product
UDP [CPD:C00015];
(S)-4-hydroxymandelonitrile beta-D-glucoside [CPD:C05143]
Comment
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].
History
EC 2.4.1.85 created 1976, modified 2005
Pathway
ec00460  Cyanoamino acid metabolism
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K13030  cyanohydrin beta-glucosyltransferase
Genes
BDI: 100843904
ATS: 109786124(LOC109786124)
SBI: 8060874
ZMA: 100284975
Reference
1  [PMID:4416442]
  Authors
Reay PF, Conn EE.
  Title
The purification and properties of a uridine diphosphate glucose: aldehyde cyanohydrin beta-glucosyltransferase from sorghum seedlings.
  Journal
J Biol Chem 249:5826-30 (1974)
Reference
2  [PMID:10585420]
  Authors
Jones PR, Moller BL, Hoj PB.
  Title
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.
  Journal
J Biol Chem 274:35483-91 (1999)
DOI:10.1074/jbc.274.50.35483
  Sequence
[sbi:8060874]
Reference
3  [PMID:12946413]
  Authors
Hansen KS, Kristensen C, Tattersall DB, Jones PR, Olsen CE, Bak S, Moller BL.
  Title
The in vitro substrate regiospecificity of recombinant UGT85B1, the cyanohydrin glucosyltransferase from Sorghum bicolor.
  Journal
Phytochemistry 64:143-51 (2003)
DOI:10.1016/S0031-9422(03)00261-9
  Sequence
[sbi:8060874]
Reference
4  [PMID:12114576]
  Authors
Busk PK, Moller BL.
  Title
Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants.
  Journal
Plant Physiol 129:1222-31 (2002)
DOI:10.1104/pp.000687
Reference
5  [PMID:15665094]
  Authors
Kristensen C, Morant M, Olsen CE, Ekstrom CT, Galbraith DW, Moller BL, Bak S.
  Title
Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome.
  Journal
Proc Natl Acad Sci U S A 102:1779-84 (2005)
DOI:10.1073/pnas.0409233102
  Sequence
[sbi:8060874]
Other DBs
ExplorEnz - The Enzyme Database: 2.4.1.85
IUBMB Enzyme Nomenclature: 2.4.1.85
ExPASy - ENZYME nomenclature database: 2.4.1.85
BRENDA, the Enzyme Database: 2.4.1.85
CAS: 55354-52-4

KEGG   REACTION: R04296
Entry
R04296                      Reaction                               

Name
UDPglucose:(S)-4-hydroxymandelonitrile beta-D-glucosyltransferase
Definition
UDP-glucose + (S)-4-Hydroxymandelonitrile <=> UDP + Dhurrin
Equation
Reaction class
RC00005  C00015_C00029
RC00397  C03742_C05143
Enzyme
Pathway
rn00460  Cyanoamino acid metabolism
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00369  Cyanogenic glycoside biosynthesis, tyrosine => dhurrin
Orthology
K13030  cyanohydrin beta-glucosyltransferase [EC:2.4.1.85]
Other DBs
RHEA: 12856

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