EC |
1.14.99.61 |
Accepted name: |
cyclooctat-9-en-7-ol 5-monooxygenase |
Reaction: |
cyclooctat-9-en-7-ol + reduced acceptor + O2 = cyclooctat-9-ene-5,7-diol + acceptor + H2O |
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For diagram of cyclooctatin biosynthesis, click here |
Glossary: |
cyclooctat-9-en-7-ol = (1S,3aS,4R,7S,9aS,10aS)-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
cyclooctat-9-ene-5,7-diol = (1S,3R,3aS,4R,7S,9aS,10aS)-1,4,9a-trimethyl-7-(propan-2-yl)-1,2,3,3a,4,5,7,8,9,9a,10,10a-dodecahydrodicyclopenta[a,d][8]annulene-3,4-diol |
Other name(s): |
CotB3 |
Systematic name: |
cyclooctat-9-en-7-ol,hydrogen-donor:oxygen oxidoreductase (5-hydroxylating) |
Comments: |
Isolated from the bacterium Streptomyces melanosporofaciens M1614-43f2. Involved in the biosynthesis of cyclooctatin. |
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. |
Gorner, C., Schrepfer, P., Redai, V., Wallrapp, F., Loll, B., Eisenreich, W., Haslbeck, M. and Bruck, T. Identification, characterization and molecular adaptation of class I redox systems for the production of hydroxylated diterpenoids. Microb. Cell Fact. 15:86 (2016). [PMID: 27216162] |
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[EC 1.14.99.61 created 2018] |
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EC |
1.14.99.62 |
Accepted name: |
cyclooctatin synthase |
Reaction: |
cyclooctat-9-ene-5,7-diol + reduced acceptor + O2 = cyclooctatin + acceptor + H2O |
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For diagram of cyclooctatin biosynthesis, click here |
Glossary: |
cyclooctat-9-ene-5,7-diol = (1S,3R,3aS,4R,7S,9aS,10aS)-1,4,9a-trimethyl-7-(propan-2-yl)-1,2,3,3a,4,5,7,8,9,9a,10,10a-dodecahydrodicyclopenta[a,d][8]annulene-3,4-diol
cyclooctatin = cycloctat-9-ene-5,7,18-triol = (1R,3R,3aS,4R,7S,9aS,10aS)-1-(hydroxymethyl-)4,9a-dimethyl-7-(propan-2-yl)-1,2,3,3a,4,5,7,8,9,9a,10,10a-dodecahydrodicyclopenta[a,d][8]annulene-3,4-diol |
Other name(s): |
CotB4 |
Systematic name: |
cyclooctat-9-ene-5,7-diol,hydrogen-donor:oxygen oxidoreductase (18-hydroxylating) |
Comments: |
Isolated from the bacterium Streptomyces melanosporofaciens M1614-43f2. |
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. |
Gorner, C., Schrepfer, P., Redai, V., Wallrapp, F., Loll, B., Eisenreich, W., Haslbeck, M. and Bruck, T. Identification, characterization and molecular adaptation of class I redox systems for the production of hydroxylated diterpenoids. Microb. Cell Fact. 15:86 (2016). [PMID: 27216162] |
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[EC 1.14.99.62 created 2018] |
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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 |
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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] |
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[EC 4.2.3.146 created 2014] |
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