Entry
Name
germacrene A hydroxylase;
GAO (gene name)
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
(+)-germacrene-A,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (12-hydroxylating)
Reaction(IUBMB)
(+)-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) [RN:
R12128 ];
(1a) (+)-germacrene A + O2 + [reduced NADPH---hemoprotein reductase] = germacra-1(10),4,11(13)-trien-12-ol + [oxidized NADPH---hemoprotein reductase] + H2O [RN:
R09549 ];
(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 [RN:
R12129 ];
(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 [RN:
R12130 ]
Reaction(KEGG)
Substrate
(+)-germacrene A [CPD:
C16141 ];
[reduced NADPH---hemoprotein reductase] [CPD:
C03024 ];
O2 [CPD:
C00007 ];
germacra-1(10),4,11(13)-trien-12-ol [CPD:
C19676 ];
germacra-1(10),4,11(13)-trien-12-al [CPD:
C19677 ]
Product
germacra-1(10),4,11(13)-trien-12-oate [CPD:
C19678 ];
[oxidized NADPH---hemoprotein reductase] [CPD:
C03161 ];
H2O [CPD:
C00001 ];
germacra-1(10),4,11(13)-trien-12-ol [CPD:
C19676 ];
germacra-1(10),4,11(13)-trien-12-al [CPD:
C19677 ]
Comment
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.
History
EC 1.14.14.95 created 2011 as EC 1.14.13.123, transferred 2018 to EC 1.14.14.95
Pathway
ec00909 Sesquiterpenoid and triterpenoid biosynthesis
ec01110 Biosynthesis of secondary metabolites
Orthology
Genes
LSV : 111882413 111906166 111906167
CCAV : 112515273 112515404 112515606
Taxonomy
Reference
Authors
Nguyen DT, Gopfert JC, Ikezawa N, Macnevin G, Kathiresan M, Conrad J, Spring O, Ro DK
Title
Biochemical conservation and evolution of germacrene A oxidase in asteraceae.
Journal
Sequence
Reference
Authors
Liu Q, Manzano D, Tanic N, Pesic M, Bankovic J, Pateraki I, Ricard L, Ferrer A, de Vos R, van de Krol S, Bouwmeester H
Title
Elucidation and in planta reconstitution of the parthenolide biosynthetic pathway.
Journal
Other DBs