Germacrene A hydroxylase

Germacrene A hydroxylase
Identifiers
EC no.1.14.14.95
Databases
BRENDAenzyme data
ExPASyNiceZyme view
KEGGenzyme entry
MetaCycmetabolic pathway
Rheareactions
PDB structuresRCSB PDB PDBe PDBsum
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PMCarticles
PubMedarticles
NCBIproteins

Germacrene A hydroxylase (EC 1.14.14.95) is an enzyme with systematic name (+)-germacrene-A,NADPH:oxygen oxidoreductase (12-hydroxylating).[1] It catalyses a sequence of three oxidation reactions.[2] The first converts (+)-germacrene A to an alcohol by addition of a hydroxy group:

2D representation of the chemical structure of Q27104477.
(+)-germacrene A
 
O2
H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27131593.
hydroxy derivative

Germacrene A hydroxylase is a cytochrome P450 protein containing heme. It requires a partner cytochrome P450 reductase for functional expression. This uses nicotinamide adenine dinucleotide phosphate. After two further oxidation steps, the product is germacrene A acid.[3]

2D representation of the chemical structure of Q27131593.
hydroxy derivative
2 steps
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q27131000.
(+)-germacrene A acid

The product is further converted in chicory plants to a sesquiterpene lactone.[3]

References

  1. ↑ Nguyen DT, Göpfert JC, Ikezawa N, Macnevin G, Kathiresan M, Conrad J, Spring O, Ro DK (May 2010). "Biochemical conservation and evolution of germacrene A oxidase in asteraceae". The Journal of Biological Chemistry. 285 (22): 16588–98. doi:10.1074/jbc.M110.111757. PMC 2878029. PMID 20351109.
  2. ↑ Enzyme 1.14.14.95 at KEGG Pathway Database.
  3. 1 2 de Kraker JW, Franssen MC, Dalm MC, de Groot A, Bouwmeester HJ (April 2001). "Biosynthesis of germacrene A carboxylic acid in chicory roots. Demonstration of a cytochrome P450 (+)-germacrene a hydroxylase and NADP+-dependent sesquiterpenoid dehydrogenase(s) involved in sesquiterpene lactone biosynthesis". Plant Physiology. 125 (4): 1930–40. doi:10.1104/pp.125.4.1930. PMC 88848. PMID 11299372.
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