Entry
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
BRITE hierarchy
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)
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
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
VUN : 114175870 114177618 114177620 114177979
CCAJ : 109791295 109794853
APRC : 113857513 113859872
MTR : 25493067 25493068 25493071
CAM : 101495474(cyp93C3) 101495803
PSAT : 127101469 127108024 127108029
VVO : 131607453 131647063 131647064
LJA : Lj4g3v0485090.1(Lj4g3v0485090.1) Lj4g3v0485100.1(Lj4g3v0485100.1) Lj4g3v0485970.1(Lj4g3v0485970.1) Lj4g3v0485980.1(Lj4g3v0485980.1) Lj4g3v0486150.1(Lj4g3v0486150.1)
LANG : 109328965 109334798 109349375
» show all
Taxonomy
Reference
Authors
Kochs G, Grisebach H.
Title
Enzymic synthesis of isoflavones.
Journal
Reference
Authors
Hashim MF, Hakamatsuka T, Ebizuka Y, Sankawa U
Title
Reaction mechanism of oxidative rearrangement of flavanone in isoflavone biosynthesis.
Journal
Reference
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
Sequence
Reference
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
Sequence
Reference
Authors
Sawada Y, Ayabe S
Title
Multiple mutagenesis of P450 isoflavonoid synthase reveals a key active-site residue.
Journal
Sequence
Other DBs