KEGG   ENZYME: 1.14.14.87
Entry
EC 1.14.14.87               Enzyme                                 

Name
2-hydroxyisoflavanone synthase;
CYP93C;
IFS;
isoflavonoid synthase
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
liquiritigenin, [reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating, aryl migration)
Reaction(IUBMB)
(1) liquiritigenin + O2 + [reduced NADPH---hemoprotein reductase] = 2,4',7-trihydroxyisoflavanone + H2O + [oxidized NADPH---hemoprotein reductase] [RN:R07777];
(2) (2S)-naringenin + O2 + [reduced NADPH---hemoprotein reductase] = 2,4',5,7-tetrahydroxyisoflavanone + H2O + [oxidized NADPH---hemoprotein reductase] [RN:R07778]
Reaction(KEGG)
R07777 R07778;
(other) R07715
Substrate
liquiritigenin [CPD:C09762];
O2 [CPD:C00007];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
(2S)-naringenin [CPD:C00509]
Product
2,4',7-trihydroxyisoflavanone [CPD:C15567];
H2O [CPD:C00001];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
2,4',5,7-tetrahydroxyisoflavanone [CPD:C12631]
Comment
A cytochrome P-450 (heme thiolate) protein found in plants. The reaction involves the migration of the 2-phenyl group of the flavanone to the 3-position of the isoflavanone. The 2-hydroxyl group is derived from the oxygen molecule. EC 4.2.1.105, 2-hydroxyisoflavanone dehydratase, acts on the products with loss of water and formation of genistein and daidzein, respectively.
History
EC 1.14.14.87 created 2011 as EC 1.14.13.136, modified 2013, transferred 2018 to EC 1.14.14.87
Pathway
ec00943  Isoflavonoid biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K13257  2-hydroxyisoflavanone synthase
Genes
GMX: 100037450(IFS1) 606705(IFS2)
GSJ: 114374378 114374486 114419594
PVU: PHAVU_003G051700g PHAVU_003G0518001 PHAVU_003G074000g
VRA: 106763981 106780381
VAR: 108332082 108333348
VUN: 114175870 114177618 114177620 114177979
CCAJ: 109791295
MTR: MTR_4g088160 MTR_4g088170 MTR_4g088195
CAM: 101495474(cyp93C3) 101495803
LJA: Lj4g3v0485090.1(Lj4g3v0485090.1) Lj4g3v0485100.1(Lj4g3v0485100.1) Lj4g3v0485970.1(Lj4g3v0485970.1) Lj4g3v0485980.1(Lj4g3v0485980.1) Lj4g3v0486150.1(Lj4g3v0486150.1)
AIP: 107631190
 » show all
Reference
1  [PMID:3956488]
  Authors
Kochs G, Grisebach H.
  Title
Enzymic synthesis of isoflavones.
  Journal
Eur J Biochem 155:311-8 (1986)
DOI:10.1111/j.1432-1033.1986.tb09492.x
Reference
2  [PMID:2226805]
  Authors
Hashim MF, Hakamatsuka T, Ebizuka Y, Sankawa U
  Title
Reaction mechanism of oxidative rearrangement of flavanone in isoflavone biosynthesis.
  Journal
FEBS Lett 271:219-22 (1990)
DOI:10.1016/0014-5793(90)80410-K
Reference
3  [PMID:10375412]
  Authors
Steele CL, Gijzen M, Qutob D, Dixon RA
  Title
Molecular characterization of the enzyme catalyzing the aryl migration reaction of isoflavonoid biosynthesis in soybean.
  Journal
Arch Biochem Biophys 367:146-50 (1999)
DOI:10.1006/abbi.1999.1238
  Sequence
[gmx:606705]
Reference
4  [PMID:12207646]
  Authors
Sawada Y, Kinoshita K, Akashi T, Aoki T, Ayabe S.
  Title
Key amino acid residues required for aryl migration catalysed by the cytochrome P450 2-hydroxyisoflavanone synthase.
  Journal
Plant J 31:555-64 (2002)
DOI:10.1046/j.1365-313X.2002.01378.x
  Sequence
Reference
5  [PMID:15809082]
  Authors
Sawada Y, Ayabe S
  Title
Multiple mutagenesis of P450 isoflavonoid synthase reveals a key active-site residue.
  Journal
Biochem Biophys Res Commun 330:907-13 (2005)
DOI:10.1016/j.bbrc.2005.03.053
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.87
IUBMB Enzyme Nomenclature: 1.14.14.87
ExPASy - ENZYME nomenclature database: 1.14.14.87
BRENDA, the Enzyme Database: 1.14.14.87

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