The Enzyme Database

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EC 1.14.14.160     
Accepted name: zealexin A1 synthase
Reaction: (S)-β-macrocarpene + 3 O2 + 3 [reduced NADPH—hemoprotein reductase] = zealexin A1 + 4 H2O + 3 [oxidized NADPH—hemoprotein reductase] (overall reaction)
(1a) (S)-β-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]
(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]
(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]
Glossary: (S)-β-macrocarpene = (1′S)-4′,5,5-trimethyl-1,1′-bi(cyclohexane)-1,3′-diene
zealexin A1 = (4S)-4-(5,5-dimethylcyclohex-1-en-1-yl)cyclohex-1-ene-1-carboxylate
Other name(s): CYP71Z18 (gene name)
Systematic name: (S)-β-macrocarpene,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (zealexin A1-forming)
Comments: A cytochrome P-450 (heme thiolate) enzyme characterized from maize. The enzyme sequentially oxidizes(S)-β-macrocarpene via alcohol and aldehyde intermediates to form zealexin A1, a maize phytoalexin that provides biochemical protection against fungal infection.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Mao, H., Liu, J., Ren, F., Peters, R.J. and Wang, Q. Characterization of CYP71Z18 indicates a role in maize zealexin biosynthesis. Phytochemistry 121 (2016) 4–10. [PMID: 26471326]
[EC 1.14.14.160 created 2018]
 
 
EC 4.2.3.55     
Accepted name: (S)-β-bisabolene synthase
Reaction: (2E,6E)-farnesyl diphosphate = (S)-β-bisabolene + diphosphate
For diagram of bisabolene biosynthesis, click here, for diagram of bisabolene biosynthesis, click here and for diagram of bisabolene and macrocarpene biosynthesis, click here
Systematic name: (2E,6E)-farnesyl-diphosphate diphosphate-lyase [(S)-β-bisabolene-forming]
Comments: The synthesis of (S)-β-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-β-bisabolene. The second step is the isomerization to (S)-β-macrocarpene (cf. EC 5.5.1.17, (S)-β-macrocarpene synthase). The enzyme requires Mg2+ or Mn2+ for activity.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Fujisawa, M., Harada, H., Kenmoku, H., Mizutani, S. and Misawa, N. Cloning and characterization of a novel gene that encodes (S)-β-bisabolene synthase from ginger, Zingiber officinale. Planta 232 (2010) 121–130. [DOI] [PMID: 20229191]
[EC 4.2.3.55 created 2011]
 
 
EC 5.5.1.17     
Accepted name: (S)-β-macrocarpene synthase
Reaction: (S)-β-bisabolene = (S)-β-macrocarpene
For diagram of biosynthesis of bicyclic sesquiterpenoids derived from bisabolyl cation, click here and for diagram of bisabolene and macrocarpene biosynthesis, click here
Other name(s): TPS6; TPS11; (S)-β-macrocarpene lyase (decyclizing)
Systematic name: (S)-β-macrocarpene lyase (ring-opening)
Comments: The synthesis of (S)-β-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-β-bisabolene (cf. EC 4.2.3.55, (S)-β-bisabolene synthase). The second step is the isomerization to (S)-β-macrocarpene.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Kollner, T.G., Schnee, C., Li, S., Svatos, A., Schneider, B., Gershenzon, J. and Degenhardt, J. Protonation of a neutral (S)-β-bisabolene intermediate is involved in (S)-β-macrocarpene formation by the maize sesquiterpene synthases TPS6 and TPS11. J. Biol. Chem. 283 (2008) 20779–20788. [DOI] [PMID: 18524777]
[EC 5.5.1.17 created 2011]
 
 


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