KEGG   ORTHOLOGY: K13257
Entry
K13257                      KO                                     
Symbol
CYP93C
Name
2-hydroxyisoflavanone synthase [EC:1.14.14.87]
Pathway
map00943  Isoflavonoid biosynthesis
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00941  Isoflavone biosynthesis, liquiritigenin/naringenin => daidzein/genistein
Reaction
R07715  6,7,4'-trihydroxyflavanone,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating, aryl migration)
R07777  liquiritigenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating, aryl migration)
R07778  naringenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating, aryl migration)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00943 Isoflavonoid biosynthesis
    K13257  CYP93C; 2-hydroxyisoflavanone synthase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K13257  CYP93C; 2-hydroxyisoflavanone synthase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.87  2-hydroxyisoflavanone synthase
     K13257  CYP93C; 2-hydroxyisoflavanone synthase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP93 family
   K13257  CYP93C; 2-hydroxyisoflavanone synthase
Other DBs
GO: 0033770
Genes
GMX: 100037450(IFS1) 121173309 606705(IFS2)
GSJ: 114374378 114374486 114419594
PVU: PHAVU_003G051700g PHAVU_003G0518001 PHAVU_003G074000g
VRA: 106763981 106780381
VAR: 108332082 108333348
VUN: 114175870 114177618 114177620 114177979
VUM: 124839830 124842155
CCAJ: 109791295 109794853
APRC: 113857513 113859872
MTR: 25493067 25493068 25493071
TPRA: 123918472
CAM: 101495474(cyp93C3) 101495803
PSAT: 127101469 127108024 127108029
VVO: 131607453 131647063 131647064
LJA: 130710769 130713579
ADU: 107480672 107480757
AIP: 107631190
AHF: 112733554 112791520
LANG: 109328965 109334798 109349375
AG: BAA76380(CYP93C2)
 » show all
Reference
PMID:10375412 (CYP93C1)
  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
PMID:10557230 (CYP93C2)
  Authors
Akashi T, Aoki T, Ayabe Si
  Title
Cloning and functional expression of a cytochrome P450 cDNA encoding 2-hydroxyisoflavanone synthase involved in biosynthesis of the isoflavonoid skeleton in licorice.
  Journal
Plant Physiol 121:821-8 (1999)
DOI:10.1104/pp.121.3.821
  Sequence
[ag:BAA76380]
LinkDB

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) 121173309 606705(IFS2)
GSJ: 114374378 114374486 114419594
PVU: PHAVU_003G051700g PHAVU_003G0518001 PHAVU_003G074000g
VRA: 106763981 106780381
VAR: 108332082 108333348
VUN: 114175870 114177618 114177620 114177979
VUM: 124839830 124842155
CCAJ: 109791295 109794853
APRC: 113857513 113859872
MTR: 25493067 25493068 25493071
TPRA: 123918472
CAM: 101495474(cyp93C3) 101495803
PSAT: 127101469 127108024 127108029
VVO: 131607453 131647063 131647064
LJA: 130710769 130713579
ADU: 107480672 107480757
AIP: 107631190
AHF: 112733554 112791520
LANG: 109328965 109334798 109349375
 » 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
[ag:BAA76380]
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
[ag:BAA76380]
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
LinkDB

KEGG   REACTION: R07778
Entry
R07778                      Reaction                               
Name
naringenin,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (hydroxylating, aryl migration)
Definition
Naringenin + Oxygen + [Reduced NADPH---hemoprotein reductase] <=> 2-Hydroxy-2,3-dihydrogenistein + H2O + [Oxidized NADPH---hemoprotein reductase]
Equation
C00509 + C00007 + C03024 <=> C12631 + C00001 + C03161
Reaction class
RC01837  C00509_C12631
Enzyme
1.14.14.87
Pathway
rn00943  Isoflavonoid biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00941  Isoflavone biosynthesis, liquiritigenin/naringenin => daidzein/genistein
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.87
     R07778  Naringenin + Oxygen + [Reduced NADPH---hemoprotein reductase] <=> 2-Hydroxy-2,3-dihydrogenistein + H2O + [Oxidized NADPH---hemoprotein reductase]
Orthology
K13257  2-hydroxyisoflavanone synthase [EC:1.14.14.87]
Other DBs
RHEA: 35490
LinkDB

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