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Literature summary for 1.14.11.36 extracted from

  • Seo, M.J.; Zhu, D.; Endo, S.; Ikeda, H.; 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 (2011), Biochemistry, 50, 1739-1754.
    View publication on PubMedView publication on EuropePMC

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
neopentalenolactone D + 2 2-oxoglutarate Streptomyces exfoliatus
-
neopentalenolactone F + methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate + ? incubation of enzyme with its natural substrate neopentalenolactone D gives a mixture of neopentalenolactone E and its derived hydrolysis product, methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate ?
neopentalenolactone D + 2 2-oxoglutarate Streptomyces arenae
-
neopentalenolactone F + methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate + ? incubation of enzyme with its natural substrate neopentalenolactone D gives a mixture of neopentalenolactone E and its derived hydrolysis product, methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate ?
neopentalenolactone D + 2 2-oxoglutarate Streptomyces exfoliatus UC5319
-
neopentalenolactone F + methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate + ? incubation of enzyme with its natural substrate neopentalenolactone D gives a mixture of neopentalenolactone E and its derived hydrolysis product, methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate ?
neopentalenolactone D + 2 2-oxoglutarate Streptomyces arenae TU469
-
neopentalenolactone F + methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate + ? incubation of enzyme with its natural substrate neopentalenolactone D gives a mixture of neopentalenolactone E and its derived hydrolysis product, methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate ?

Organism

Organism UniProt Comment Textmining
Streptomyces arenae E3VWI8
-
-
Streptomyces arenae TU469 E3VWI8
-
-
Streptomyces exfoliatus E3VWK4
-
-
Streptomyces exfoliatus UC5319 E3VWK4
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
neopentalenolactone D + 2 2-oxoglutarate
-
Streptomyces exfoliatus neopentalenolactone F + methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate + ? incubation of enzyme with its natural substrate neopentalenolactone D gives a mixture of neopentalenolactone E and its derived hydrolysis product, methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate ?
neopentalenolactone D + 2 2-oxoglutarate
-
Streptomyces arenae neopentalenolactone F + methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate + ? incubation of enzyme with its natural substrate neopentalenolactone D gives a mixture of neopentalenolactone E and its derived hydrolysis product, methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate ?
neopentalenolactone D + 2 2-oxoglutarate
-
Streptomyces exfoliatus UC5319 neopentalenolactone F + methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate + ? incubation of enzyme with its natural substrate neopentalenolactone D gives a mixture of neopentalenolactone E and its derived hydrolysis product, methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate ?
neopentalenolactone D + 2 2-oxoglutarate
-
Streptomyces arenae TU469 neopentalenolactone F + methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate + ? incubation of enzyme with its natural substrate neopentalenolactone D gives a mixture of neopentalenolactone E and its derived hydrolysis product, methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate ?
pentalenolactone D + 2 2-oxoglutarate
-
Streptomyces exfoliatus pentalenolactone F + 2 succinate + 2 CO2 + H2O
-
?
pentalenolactone D + 2 2-oxoglutarate
-
Streptomyces arenae pentalenolactone F + 2 succinate + 2 CO2 + H2O
-
?
pentalenolactone D + 2 2-oxoglutarate
-
Streptomyces exfoliatus UC5319 pentalenolactone F + 2 succinate + 2 CO2 + H2O
-
?
pentalenolactone D + 2 2-oxoglutarate
-
Streptomyces arenae TU469 pentalenolactone F + 2 succinate + 2 CO2 + H2O
-
?

Synonyms

Synonyms Comment Organism
penD
-
Streptomyces exfoliatus
penD
-
Streptomyces arenae

General Information

General Information Comment Organism
physiological function enzyme deletion mutants accumulate pentalenolactone D but are blocked in production of pentalenolactone as well as the precursors pentalenolactones E and F. Analysis of the gene cluster responsible for pentalenolactone synthesis. Reaction starts with the flavin-dependent Baeyer-Villiger oxidation of 1-deoxy-11-oxopentalenic acid to pentalenolactone D followed by the two-stage Fe2+-alpha-ketoglutarate-dependent oxidation to pentalenolactones E and F, catalyzed by the enzyme, PntD. Incubation of PntD with its natural substrate neopentalenolactone D gives a mixture of neopentalenolactone E and its derived hydrolysis product, methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate Streptomyces arenae
physiological function enzyme deletion mutants accumulate pentalenolactone D but are blocked in production of pentalenolactone as well as the precursors pentalenolactones E and F. Analysis of the gene cluster responsible for pentalenolactone synthesis. Reaction starts with the flavin-dependent Baeyer-Villiger oxidation of 1-deoxy-11-oxopentalenic acid to pentalenolactone D followed by the two-stage Fe2+-alpha-ketoglutarate-dependent oxidation to pentalenolactones E and F, catalyzed by the enzyme, PtlD. Incubation of PtlD with its natural substrate neopentalenolactone D gives a mixture of neopentalenolactone E and its derived hydrolysis product, methyl (1R,6aR)-6a-acetyl-1-(2-methoxy-2-oxoethyl)-5,5-dimethyl-1,3a,4,5,6,6a-hexahydropentalene-2-carboxylate Streptomyces exfoliatus