Reaction: (+)-germacrene A + 3 [reduced NADPH—hemoprotein reductase] + 3 O2 = germacra-1(10),4,11(13)-trien-12-oate + 3 [oxidized NADPH—hemoprotein reductase] + 4 H2O (overall reaction)
(1a) (+)-germacrene A + O2 + [reduced NADPH—hemoprotein reductase] = germacra-1(10),4,11(13)-trien-12-ol + [oxidized NADPH—hemoprotein reductase] + H2O
(1b) germacra-1(10),4,11(13)-trien-12-ol + O2 + [reduced NADPH—hemoprotein reductase] = germacra-1(10),4,11(13)-trien-12-al + [oxidized NADPH—hemoprotein reductase] + 2 H2O
(1c) germacra-1(10),4,11(13)-trien-12-al + O2 + [reduced NADPH—hemoprotein reductase] = germacra-1(10),4,11(13)-trien-12-oate + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of reaction click here.
Other name(s): GAO (gene name)
Systematic name: (+)-germacrene-A,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (12-hydroxylating)
Comments: A cytochrome P-450 (heme-thiolate) protein. This plant enzyme catalyses three steps in a pathway that leads to the biosynthesis of many sesquiterpenoid lactones.
Links to other databases: BRENDA, EXPASY, KEGG, Metacyc, CAS registry number:
References:
1. Nguyen, D.T., Gopfert, J.C., Ikezawa, N., Macnevin, G., Kathiresan, M., Conrad, J., Spring, O. and Ro, D.K. Biochemical conservation and evolution of germacrene A oxidase in asteraceae. J. Biol. Chem. 285 (2010) 16588-16598. [PMID: 20351109]
2. Liu, Q., Manzano, D., Tanic, N., Pesic, M., Bankovic, J., Pateraki, I., Ricard, L., Ferrer, A., de Vos, R., van de Krol, S. and Bouwmeester, H. Elucidation and in planta reconstitution of the parthenolide biosynthetic pathway. Metab. Eng. 23 (2014) 145-153. [PMID: 24704560]