KEGG   ENZYME: 1.14.14.160
Entry
EC 1.14.14.160              Enzyme                                 

Name
zealexin A1 synthase;
CYP71Z18 (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
Sysname
(S)-beta-macrocarpene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (zealexin A1-forming)
Reaction(IUBMB)
(S)-beta-macrocarpene + 3 O2 + 3 [reduced NADPH---hemoprotein reductase] = zealexin A1 + 4 H2O + 3 [oxidized NADPH---hemoprotein reductase] (overall reaction) [RN:R12226];
(1a) (S)-beta-macrocarpene + O2 + [reduced NADPH---hemoprotein reductase] = [(4S)-4-(5,5-dimethylcyclohex-1-en-1-yl)-cyclohex-1-en-1-yl]methanol + H2O + [oxidized NADPH---hemoprotein reductase] [RN:R12227];
(1b) [(4S)-4-(5,5-dimethylcyclohex-1-en-1-yl)-cyclohex-1-en-1-yl] methanol + O2 + [reduced NADPH---hemoprotein reductase] = (4S)-4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + 2 H2O + [oxidized NADPH---hemoprotein reductase] [RN:R12228];
(1c) (4S)-4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde + O2 + [reduced NADPH---hemoprotein reductase] = zealexin A1 + H2O + [oxidized NADPH---hemoprotein reductase] [RN:R12229]
Reaction(KEGG)
Substrate
(S)-beta-macrocarpene [CPD:C19752];
O2 [CPD:C00007];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
[(4S)-4-(5,5-dimethylcyclohex-1-en-1-yl)-cyclohex-1-en-1-yl] methanol;
(4S)-4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde [CPD:C22013]
Product
zealexin A1 [CPD:C22011];
H2O [CPD:C00001];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
[(4S)-4-(5,5-dimethylcyclohex-1-en-1-yl)-cyclohex-1-en-1-yl]methanol [CPD:C22012];
(4S)-4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carbaldehyde [CPD:C22013]
Comment
A cytochrome P-450 (heme thiolate) enzyme characterized from maize. The enzyme sequentially oxidizes(S)-beta-macrocarpene via alcohol and aldehyde intermediates to form zealexin A1, a maize phytoalexin that provides biochemical protection against fungal infection.
History
EC 1.14.14.160 created 2018
Orthology
K23134  dolabradiene monooxygenase / zealexin A1 synthase
Genes
ZMA: 100273457 103628119
Reference
1  [PMID:26471326]
  Authors
Mao H, Liu J, Ren F, Peters RJ, Wang Q
  Title
Characterization of CYP71Z18 indicates a role in maize zealexin biosynthesis.
  Journal
Phytochemistry 121:4-10 (2016)
DOI:10.1016/j.phytochem.2015.10.003
  Sequence
[zma:100273457]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.160
IUBMB Enzyme Nomenclature: 1.14.14.160
ExPASy - ENZYME nomenclature database: 1.14.14.160
BRENDA, the Enzyme Database: 1.14.14.160

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