Reaction: liquiritigenin + O2 + NADPH + H+ = 2,7,4'-trihydroxyisoflavanone + H2O + NADP+
For diagram of reaction click here.
Glossary: liquiritigenin = 7,4'-dihydroxyflavanone
Other name(s): CYT93C; IFS; 2-hydroxyisoflavanone synthase (ambiguous)
Systematic name: liquiritigenin,NADPH:oxygen oxidoreductase (hydroxylating, aryl migration)
Comments: Requires cytochrome P450. The reaction involves the migration of the 2-phenyl group of the flavanone liquiritigenin to the 3-position of the isoflavanone. The 2-hydroxyl group is derived from the oxygen molecule.
Links to other databases: BRENDA, EXPASY, KEGG, CAS registry number:
References:
1. Hashim, M.F., Hakamatsuka, T., Ebizuka, Y. and Sankawa, U. Reaction mechanism of oxidative rearrangement of flavanone in isoflavone biosynthesis. FEBS Lett. 271 (1990) 219-222. [PMID: 2226805]
2. Sawada, Y., Kinoshita, K., Akashi, T., Aoki, T. and Ayabe, S. Key amino acid residues required for aryl migration catalysed by the cytochrome P450 2-hydroxyisoflavanone synthase. Plant J. 31 (2002) 555-564. [PMID: 12207646]
3. Sawada, Y. and Ayabe, S. Multiple mutagenesis of P450 isoflavonoid synthase reveals a key active-site residue. Biochem. Biophys. Res. Commun. 330 (2005) 907-913. [PMID: 15809082]