Reaction: geranylgeranyl diphosphate = isoelisabethatriene + diphosphate
For diagram of reaction click here or mechanism click here.
Glossary: isoelisabethatriene = (1S,4R)-4,7-dimethyl-1-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,4,5,6-hexahydronaphthalene
Other name(s): HpS (ambiguous)
Systematic name: geranylgeranyl-diphosphate diphosphate-lyase (cyclizing, isoelisabethatriene-forming)
Comments: Isolated from the bacterium Streptomyces clavuligerus. The 1-proR hydrogen atom of geranylgeranyl diphosphate is involved in a 1,3-hydride shift to the side-chain. The enzyme also produces hydropyrene, hydropyrenol, and traces of other diterpenoids. cf. EC 4.2.3.201, hydropyrene synthase, and EC 4.2.3.202, hydropyrenol synthase.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number:
References:
1. Rinkel, J., Rabe, P., Chen, X., Kollner, T.G., Chen, F. and Dickschat, J.S. Mechanisms of the diterpene cyclases β-pinacene synthase from Dictyostelium discoideum and hydropyrene synthase from Streptomyces clavuligerus. Chem. Eur. J. 23 (2017) 10501-10505. [PMID: 28696553]