|Superclasses:||Reactions Classified By Conversion Type → Simple Reactions → Chemical Reactions|
|Reactions Classified By Substrate → Small-Molecule Reactions|
EC Number: 184.108.40.206
In Pathway: terpentecin biosynthesis
The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.
Mass balance status: Balanced.
Enzyme Commission Primary Name: terpentedienyl-diphosphate synthase
Enzyme Commission Synonyms: terpentedienol diphosphate synthase, Cyc1, clerodadienyl diphosphate synthase
Standard Gibbs Free Energy (ΔrG'° in kcal/mol): -56.66 [Latendresse13]
Enzyme Commission Summary:
Requires Mg2+. Contains a DXDD motif, which is a characteristic of diterpene cylases whose reactions are initiated by protonation at the 14,15-double bond of geranylgeranyl diphosphate (GGDP) [Hamano02]. The triggering proton is lost at the end of the cyclization reaction [Eguchi03a]. The product of the reaction, terpentedienyl diphosphate, is the substrate for EC 220.127.116.11, terpentetriene synthase and is a precursor of the diterpenoid antibiotic terpentecin.
Unification Links: Rhea:25616
Dairi01: Dairi T, Hamano Y, Kuzuyama T, Itoh N, Furihata K, Seto H (2001). "Eubacterial diterpene cyclase genes essential for production of the isoprenoid antibiotic terpentecin." J Bacteriol 183(20);6085-94. PMID: 11567009
Eguchi03a: Eguchi T, Dekishima Y, Hamano Y, Dairi T, Seto H, Kakinuma K (2003). "A new approach for the investigation of isoprenoid biosynthesis featuring pathway switching, deuterium hyperlabeling, and 1H NMR spectroscopy. The reaction mechanism of a novel streptomyces diterpene cyclase." J Org Chem 68(14);5433-8. PMID: 12839434
Hamano02: Hamano Y, Kuzuyama T, Itoh N, Furihata K, Seto H, Dairi T (2002). "Functional analysis of eubacterial diterpene cyclases responsible for biosynthesis of a diterpene antibiotic, terpentecin." J Biol Chem 277(40);37098-104. PMID: 12138123
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