KEGG   ORTHOLOGY: K13265
Entry
K13265                      KO                                     
Symbol
VR
Name
vestitone reductase [EC:1.1.1.348]
Pathway
map00943  Isoflavonoid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00942  Pterocarpan biosynthesis, daidzein => medicarpin
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00943 Isoflavonoid biosynthesis
    K13265  VR; vestitone reductase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.1  Acting on the CH-OH group of donors
   1.1.1  With NAD+ or NADP+ as acceptor
    1.1.1.348  (3R)-2'-hydroxyisoflavanone reductase
     K13265  VR; vestitone reductase
Other DBs
RN: R07737
Genes
GMX: 100194416 100793687 100794209 547660
GSJ: 114394465 114394525 114425491 114425668
PVU: PHAVU_008G076600g PHAVU_008G076700g
VRA: 106779595
VAR: 108328041
VUN: 114183399 114184905
CCAJ: 109802944
APRC: 113866729
MTR: MTR_7g074710
CAM: 101514431
LJA: Lj6g3v0294050.1(Lj6g3v0294050.1)
 » show all
Reference
PMID:7625843
  Authors
Guo L, Paiva NL
  Title
Molecular cloning and expression of alfalfa (Medicago sativa L.) vestitone reductase, the penultimate enzyme in medicarpin biosynthesis.
  Journal
Arch Biochem Biophys 320:353-60 (1995)
DOI:10.1016/0003-9861(95)90019-5
  Sequence

KEGG   ENZYME: 1.1.1.348
Entry
EC 1.1.1.348                Enzyme                                 
Name
(3R)-2'-hydroxyisoflavanone reductase;
vestitone reductase;
pterocarpin synthase (incorrect);
pterocarpan synthase (incorrect)
Class
Oxidoreductases;
Acting on the CH-OH group of donors;
With NAD+ or NADP+ as acceptor
Sysname
(3R)-2'-hydroxyisoflavanone:NADP+ 4-oxidoreductase
Reaction(IUBMB)
a (4R)-4,2'-dihydroxyisoflavan + NADP+ = a (3R)-2'-hydroxyisoflavanone + NADPH + H+ [RN:R11877]
Reaction(KEGG)
R11877 > R07737
Substrate
(4R)-4,2'-dihydroxyisoflavan [CPD:C21738];
NADP+ [CPD:C00006]
Product
(3R)-2'-hydroxyisoflavanone [CPD:C21739];
NADPH [CPD:C00005];
H+ [CPD:C00080]
Comment
This plant enzyme participates in the biosynthesis of the pterocarpan phytoalexins medicarpin, maackiain, and several forms of glyceollin. The enzyme has a strict stereo specificity for the 3R-isoflavanones.
History
EC 1.1.1.348 created 1992 as EC 1.1.1.246, part transferred 2013 to EC 1.1.1.348
Pathway
ec00943  Isoflavonoid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K13265  vestitone reductase
Genes
GMX100194416 100793687 100794209 547660
GSJ114394465 114394525 114425491 114425668
PVUPHAVU_008G076600g PHAVU_008G076700g
VRA106779595
VAR108328041
VUN114183399 114184905
CCAJ109802944
APRC113866729
MTRMTR_7g074710
CAM101514431
LJALj6g3v0294050.1(Lj6g3v0294050.1)
ADU107472037 107485391
AIP107624299 107638006
AHF112716970 112728283 112740569 112753158 112784826 112794395
 » show all
Reference
1
  Authors
Bless, W. and Barz, W.
  Title
Isolation of pterocarpan synthase, the terminal enzyme of pterocarpan phytoalexin biosynthesis in cell-suspension cultures of Cicer arietinum.
  Journal
FEBS Lett 235:47-50 (1988)
Reference
2  [PMID:8071365]
  Authors
Guo L, Dixon RA, Paiva NL.
  Title
Conversion of vestitone to medicarpin in alfalfa (Medicago sativa L.) is catalyzed by two independent enzymes. Identification, purification, and characterization of vestitone reductase and 7,2'-dihydroxy-4'-methoxyisoflavanol  dehydratase.
  Journal
J Biol Chem 269:22372-8 (1994)
  Sequence
Reference
3  [PMID:7805842]
  Authors
Guo L, Dixon RA, Paiva NL
  Title
The 'pterocarpan synthase' of alfalfa: association and co-induction of vestitone  reductase and 7,2'-dihydroxy-4'-methoxy-isoflavanol (DMI) dehydratase, the two final enzymes in medicarpin biosynthesis.
  Journal
FEBS Lett 356:221-5 (1994)
DOI:10.1016/0014-5793(94)01267-9
  Sequence
Reference
4  [PMID:7625843]
  Authors
Guo L, Paiva NL
  Title
Molecular cloning and expression of alfalfa (Medicago sativa L.) vestitone reductase, the penultimate enzyme in medicarpin biosynthesis.
  Journal
Arch Biochem Biophys 320:353-60 (1995)
DOI:10.1016/0003-9861(95)90019-5
  Sequence
Reference
5  [PMID:17433362]
  Authors
Shao H, Dixon RA, Wang X
  Title
Crystal structure of vestitone reductase from alfalfa (Medicago sativa L.).
  Journal
J Mol Biol 369:265-76 (2007)
DOI:10.1016/j.jmb.2007.03.040
Other DBs
ExplorEnz - The Enzyme Database: 1.1.1.348
IUBMB Enzyme Nomenclature: 1.1.1.348
ExPASy - ENZYME nomenclature database: 1.1.1.348
BRENDA, the Enzyme Database: 1.1.1.348
CAS: 118477-70-6

KEGG   REACTION: R07737
Entry
R07737                      Reaction                               
Name
(3R,4R)-4'-methoxyisoflavan-2',4,7-triol:NADP+ 4-oxidoreductase
Definition
(-)-Vestitone + NADPH + H+ <=> 7,2'-Dihydroxy-4'-methoxy-isoflavanol + NADP+
Equation
Comment
vestitione reductase
Reaction class
RC00001  C00005_C00006
RC00235  C00786_C16187
Enzyme
Pathway
rn00943  Isoflavonoid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00942  Pterocarpan biosynthesis, daidzein => medicarpin
Orthology
K13265  vestitone reductase [EC:1.1.1.348]
Other DBs
RHEA: 35406

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