EC |
1.14.11.36 |
Accepted name: |
pentalenolactone F synthase |
Reaction: |
pentalenolactone D + 2 2-oxoglutarate + 2 O2 = pentalenolactone F + 2 succinate + 2 CO2 + H2O (overall reaction) (1a) pentalenolactone D + 2-oxoglutarate + O2 = pentalenolactone E + succinate + CO2 + H2O (1b) pentalenolactone E + 2-oxoglutarate + O2 = pentalenolactone F + succinate + CO2 |
Glossary: |
pentalenolactone D = (1S,4aR,6aS,9aR)-1,8,8-trimethyl-2-oxo-1,2,4,4a,6a,7,8,9-octahydropentaleno[1,6a-c]pyran-5-carboxylate
pentalenolactone E = (4aR,6aS,9aR)-8,8-dimethyl-1-methylene-2-oxo-1,2,4,4a,6a,7,8,9-octahydropentaleno[1,6a-c]pyran-5-carboxylate
pentalenolactone F = (1′R,4′aR,6′aS,9′aR)-8′,8′-dimethyl-2′-oxo-4′,4′a,6′a,8′,9′-hexahydrospiro[oxirane-2,1′-pentaleno[1,6a-c]pyran]-5′-carboxylic acid |
Other name(s): |
penD (gene name); pntD (gene name); ptlD (gene name) |
Systematic name: |
pentalenolactone-D,2-oxoglutarate:oxygen oxidoreductase |
Comments: |
Requires Fe(II) and ascorbate. Isolated from the bacteria Streptomyces exfoliatus, Streptomyces arenae and Streptomyces avermitilis. Part of the pentalenolactone biosynthesis pathway. |
References: |
1. |
Seo, M.J., Zhu, D., Endo, S., Ikeda, H. and Cane, D.E. Genome mining in Streptomyces. Elucidation of the role of Baeyer-Villiger monooxygenases and non-heme iron-dependent dehydrogenase/oxygenases in the final steps of the biosynthesis of pentalenolactone and neopentalenolactone. Biochemistry 50 (2011) 1739–1754. [PMID: 21250661] |
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[EC 1.14.11.36 created 2012] |
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EC |
1.14.13.170 |
Accepted name: |
pentalenolactone D synthase |
Reaction: |
1-deoxy-11-oxopentalenate + NADPH + H+ + O2 = pentalenolactone D + NADP+ + H2O |
Glossary: |
1-deoxy-11-oxopentalenate = (1S,3aR,5aS)-1,7,7-trimethyl-2-oxo-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene-4-carboxylate
pentalenolactone D = (1S,4aR,6aS,9aR)-1,8,8-trimethyl-2-oxo-1,2,4,4a,6a,7,8,9-octahydropentaleno[1,6a-c]pyran-5-carboxylate |
Other name(s): |
penE (gene name); pntE (gene name) |
Systematic name: |
1-deoxy-11-oxopentalenate,NADH:oxygen oxidoreductase (pentalenolactone-D-forming) |
Comments: |
A FAD-dependent oxygenase. Isolated from the bacteria Streptomyces exfoliatus and Streptomyces arenae. The ketone undergoes a biological Baeyer-Villiger reaction. Part of the pathway of pentalenolactone biosynthesis. |
References: |
1. |
Seo, M.J., Zhu, D., Endo, S., Ikeda, H. and Cane, D.E. Genome mining in Streptomyces. Elucidation of the role of Baeyer-Villiger monooxygenases and non-heme iron-dependent dehydrogenase/oxygenases in the final steps of the biosynthesis of pentalenolactone and neopentalenolactone. Biochemistry 50 (2011) 1739–1754. [PMID: 21250661] |
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[EC 1.14.13.170 created 2012] |
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EC |
1.14.13.171 |
Accepted name: |
neopentalenolactone D synthase |
Reaction: |
1-deoxy-11-oxopentalenate + NADPH + H+ + O2 = neopentalenolactone D + NADP+ + H2O |
Glossary: |
1-deoxy-11-oxopentalenate = (1S,3aR,5aS)-1,7,7-trimethyl-2-oxo-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene-4-carboxylate
neopentalenolactone D = (1S,4aR,6aS)-1,7,7-trimethyl-3-oxo-4,4a,6a,7,8,9-hexahydro-3H-pentaleno[6a,1-c]pyran-5-carboxylate |
Other name(s): |
ptlE (gene name) |
Systematic name: |
1-deoxy-11-oxopentalenate,NADH:oxygen oxidoreductase (neopentalenolactone-D-forming) |
Comments: |
A FAD-dependent oxygenase. Isolated from the bacterium Streptomyces avermitilis. The ketone undergoes a biological Baeyer-Villiger reaction. |
References: |
1. |
Seo, M.J., Zhu, D., Endo, S., Ikeda, H. and Cane, D.E. Genome mining in Streptomyces. Elucidation of the role of Baeyer-Villiger monooxygenases and non-heme iron-dependent dehydrogenase/oxygenases in the final steps of the biosynthesis of pentalenolactone and neopentalenolactone. Biochemistry 50 (2011) 1739–1754. [PMID: 21250661] |
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[EC 1.14.13.171 created 2012] |
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