KEGG   ORTHOLOGY: K25075
Entry
K25075                      KO                                     
Symbol
PTS
Name
pterocarpan synthase [EC:4.2.1.139]
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
    K25075  PTS; pterocarpan synthase
Enzymes [BR:ko01000]
 4. Lyases
  4.2  Carbon-oxygen lyases
   4.2.1  Hydro-lyases
    4.2.1.139  pterocarpan synthase
     K25075  PTS; pterocarpan synthase
Other DBs
RN: R07738
GO: 0050229
Genes
GMX: 100500621(PTS1) 100817155(PTS3) 100817686(PTS4)
GSJ: 114399619 114399676 114406806 114406807
PVU: PHAVU_001G145600g
VRA: 106757395 106757413 106757427
VAR: 108328428 108328436
VUN: 114178337 114193911
CCAJ: 109797846
APRC: 113862134 113863229
MTR: MTR_7g093820 MTR_7g093830 MTR_7g093850
CAM: 101491323
LJA: Lj1g3v4383290.1(Lj1g3v4383290.1)
ADU: 107492865
AIP: 107645384
 » show all
Reference
  Authors
Uchida K, Akashi T, Aoki T
  Title
The Missing Link in Leguminous Pterocarpan Biosynthesis is a Dirigent Domain-Containing Protein with Isoflavanol Dehydratase Activity.
  Journal
Plant Cell Physiol 58:398-408 (2017)
DOI:10.1093/pcp/pcw213
  Sequence

KEGG   ENZYME: 4.2.1.139
Entry
EC 4.2.1.139                Enzyme                                 
Name
pterocarpan synthase;
medicarpin synthase;
medicarpan synthase;
7,2'-dihydroxy-4'-methoxyisoflavanol dehydratase;
2',7-dihydroxy-4'-methoxyisoflavanol dehydratase;
DMI dehydratase;
DMID;
2'-hydroxyisoflavanol 4,2'-dehydratase;
PTS (gene name);
4'-methoxyisoflavan-2',4,7-triol hydro-lyase [(-)-medicarpin-forming]
Class
Lyases;
Carbon-oxygen lyases;
Hydro-lyases
Sysname
(4R)-4,2'-dihydroxyisoflavan hydro-lyase (pterocarpan-forming)
Reaction(IUBMB)
a (4R)-4,2'-dihydroxyisoflavan = a pterocarpan + H2O [RN:R12307]
Reaction(KEGG)
R12307 > R07738
Substrate
(4R)-4,2'-dihydroxyisoflavan [CPD:C21738]
Product
pterocarpan [CPD:C22071];
H2O [CPD:C00001]
Comment
The enzyme catalyses the formation of the additional ring in pterocarpan, the basic structure of phytoalexins produced by leguminous plants, including (-)-medicarpin, (+)-medicarpin, (-)-maackiain and (+)-maackiain. The enzyme requires that the hydroxyl group at C-4 of the substrate is in the (4R) configuration. The configuration of the hydrogen atom at C-3 determines whether the pterocarpan is the (+)- or (-)-enantiomer. The enzyme contains amino acid motifs characteristic of dirigent proteins.
History
EC 4.2.1.139 created 2013, modified 2019
Pathway
ec00943  Isoflavonoid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K25075  pterocarpan synthase
Genes
GMX100500621(PTS1) 100817155(PTS3) 100817686(PTS4)
GSJ114399619 114399676 114406806 114406807
PVUPHAVU_001G145600g
VRA106757395 106757413 106757427
VAR108328428 108328436
VUN114178337 114193911
CCAJ109797846
APRC113862134 113863229
MTRMTR_7g093820 MTR_7g093830 MTR_7g093850
CAM101491323
LJALj1g3v4383290.1(Lj1g3v4383290.1)
ADU107492865
AIP107645384
AHF112696146 112758883
 » show all
Reference
1  [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
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)
Reference
3  [PMID:28394400]
  Authors
Uchida K, Akashi T, Aoki T
  Title
The Missing Link in Leguminous Pterocarpan Biosynthesis is a Dirigent Domain-Containing Protein with Isoflavanol Dehydratase Activity.
  Journal
Plant Cell Physiol 58:398-408 (2017)
DOI:10.1093/pcp/pcw213
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 4.2.1.139
IUBMB Enzyme Nomenclature: 4.2.1.139
ExPASy - ENZYME nomenclature database: 4.2.1.139
BRENDA, the Enzyme Database: 4.2.1.139

KEGG   REACTION: R07738
Entry
R07738                      Reaction                               
Name
4'-methoxyisoflavan-2',4,7-triol hydro-lyase [(-)-medicarpin-forming]
Definition
7,2'-Dihydroxy-4'-methoxy-isoflavanol <=> Medicarpin + H2O
Equation
Reaction class
RC02041  C10503_C16187
Enzyme
Pathway
rn00943  Isoflavonoid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00942  Pterocarpan biosynthesis, daidzein => medicarpin
Orthology
K25075  pterocarpan synthase [EC:4.2.1.139]
Other DBs
RHEA: 35814

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