EC 1.14.14.87 - 2-hydroxyisoflavanone synthase

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IntEnz Enzyme Nomenclature
EC 1.14.14.87

Names

Accepted name:
2-hydroxyisoflavanone synthase
Other names:
CYT93C
IFS
isoflavonoid synthase
Systematic name:
liquiritigenin, [reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (hydroxylating, aryl migration)

Reactions

Comments:

A cytochrome P450 (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.

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , DIAGRAM , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway
Structural data: CSA , EC2PDB
UniProtKB/Swiss-Prot:

References

  1. Kochs, G., Grisebach, H.
    Enzymic synthesis of isoflavones.
    Eur. J. Biochem. 155: 311-318 (1986). [PMID: 3956488]
  2. Hashim, M. F., Hakamatsuka, T., Ebizuka, Y., Sankawa, U.
    Reaction mechanism of oxidative rearrangement of flavanone in isoflavone biosynthesis.
    FEBS Lett. 271: 219-222 (1990). [PMID: 2226805]
  3. Steele, C. L., Gijzen, M., Qutob, D., Dixon, R. A.
    Molecular characterization of the enzyme catalyzing the aryl migration reaction of isoflavonoid biosynthesis in soybean.
    Arch. Biochem. Biophys. 367: 146-150 (1999). [PMID: 10375412]
  4. Sawada, Y., Kinoshita, K., Akashi, T., Aoki, T., Ayabe, S.
    Key amino acid residues required for aryl migration catalysed by the cytochrome P450 2-hydroxyisoflavanone synthase.
    Plant J. 31: 555-564 (2002). [PMID: 12207646]
  5. Sawada, Y., Ayabe, S.
    Multiple mutagenesis of P450 isoflavonoid synthase reveals a key active-site residue.
    Biochem. Biophys. Res. Commun. 330: 907-913 (2005). [PMID: 15809082]

[EC 1.14.14.87 created 2011 as EC 1.14.13.136, modified 2013, transferred 2018 to EC 1.14.14.87]