The Enzyme Database

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EC 4.2.3.146     
Accepted name: cyclooctat-9-en-7-ol synthase
Reaction: geranylgeranyl diphosphate + H2O = cyclooctat-9-en-7-ol + diphosphate
For diagram of biosynthesis of fusicoccane diterpenoids, click here
Glossary: cyclooctat-9-en-7-ol = (1R,3aR,4S,7R,9aR,10aR)-1,4,9a-trimethyl-7-(propan-2-yl)-1,2,3,3a,4,5,7,8,9,9a,10,10a-dodecahydrodicyclopenta[a,d][8]annulen-4-ol
Other name(s): cotB2
Systematic name: geranylgeranyl-diphosphate diphosphate-lyase (cyclooctat-9-en-7-ol-forming)
Comments: Requires Mg2+. Isolated from the bacterium Streptomyces melanosporofaciens, where it is part of the biosynthesis of cyclooctatin, a potent inhibitor of lysophospholipase.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Kim, S.Y., Zhao, P., Igarashi, M., Sawa, R., Tomita, T., Nishiyama, M. and Kuzuyama, T. Cloning and heterologous expression of the cyclooctatin biosynthetic gene cluster afford a diterpene cyclase and two P450 hydroxylases. Chem. Biol. 16 (2009) 736–743. [DOI] [PMID: 19635410]
2.  Zhang, X., Shang, G., Gu, L. and Shen, Y. Crystallization and preliminary X-ray diffraction analysis of the diterpene cyclooctatin synthase (CYC) from Streptomyces sp. LZ35. Acta Crystallogr. F Struct. Biol. Commun. 70 (2014) 366–369. [DOI] [PMID: 24598929]
3.  Janke, R., Gorner, C., Hirte, M., Bruck, T. and Loll, B. The first structure of a bacterial diterpene cyclase: CotB2. Acta Crystallogr. D Biol. Crystallogr. 70 (2014) 1528–1537. [DOI] [PMID: 24914964]
4.  Meguro, A., Motoyoshi, Y., Teramoto, K., Ueda, S., Totsuka, Y., Ando, Y., Tomita, T., Kim, S.Y., Kimura, T., Igarashi, M., Sawa, R., Shinada, T., Nishiyama, M. and Kuzuyama, T. An unusual terpene cyclization mechanism involving a carbon-carbon bond rearrangement. Angew Chem Int Ed Engl 54 (2015) 4353–4356. [DOI] [PMID: 25689152]
5.  Tomita, T., Kim, S.Y., Teramoto, K., Meguro, A., Ozaki, T., Yoshida, A., Motoyoshi, Y., Mori, N., Ishigami, K., Watanabe, H., Nishiyama, M. and Kuzuyama, T. Structural Insights into the CotB2-catalyzed cyclization of geranylgeranyl diphosphate to the diterpene cyclooctat-9-en-7-ol. ACS Chem. Biol. 12 (2017) 1621–1628. [DOI] [PMID: 28463490]
[EC 4.2.3.146 created 2014]
 
 


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