ExplorEnz: EC 4.2.3.146

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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, PDB

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]