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Literature summary extracted from
- 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.
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 1.14.13.170 | expressed in Escherichia coli BL21(DE3) cells | Streptomyces exfoliatus |
| 1.14.13.170 | expressed in Escherichia coli BL21(DE3) cells | Streptomyces arenae |
Molecular Weight [Da]
| EC Number | Molecular Weight [Da] | Molecular Weight Maximum [Da] | Comment | Organism |
|---|---|---|---|---|
| 1.14.13.170 | 66915 | - |
x * 66915, His6-tagged enzyme, MALDI-TOF mass spectrometry | Streptomyces arenae |
| 1.14.13.170 | 67480 | - |
x * 67480, His6-tagged enzyme, MALDI-TOF mass spectrometry | Streptomyces exfoliatus |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.11.36 | 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 | ? |  |
| 1.14.11.36 | 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 | ? | |
| 1.14.11.36 | 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 | ? | |
| 1.14.11.36 | 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
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.14.11.36 | Streptomyces arenae | E3VWI8 | - |
- |
| 1.14.11.36 | Streptomyces arenae TU469 | E3VWI8 | - |
- |
| 1.14.11.36 | Streptomyces exfoliatus | E3VWK4 | - |
- |
| 1.14.11.36 | Streptomyces exfoliatus UC5319 | E3VWK4 | - |
- |
| 1.14.13.170 | Streptomyces arenae | - |
- |
- |
| 1.14.13.170 | Streptomyces arenae TU46 | - |
- |
- |
| 1.14.13.170 | Streptomyces exfoliatus | - |
- |
- |
| 1.14.13.170 | Streptomyces exfoliatus UC5319 | - |
- |
- |
| 1.14.13.171 | Streptomyces arenae | - |
- |
- |
| 1.14.13.171 | Streptomyces arenae TUE469 | - |
- |
- |
| 1.14.13.171 | Streptomyces avermitilis | - |
- |
- |
| 1.14.13.171 | Streptomyces exfoliatus | - |
- |
- |
| 1.14.13.171 | Streptomyces exfoliatus UC5319 | - |
- |
- |
Purification (Commentary)
| EC Number | Purification (Comment) | Organism |
|---|---|---|
| 1.14.13.170 | Ni-NTA column chromatography | Streptomyces exfoliatus |
| 1.14.13.170 | Ni-NTA column chromatography | Streptomyces arenae |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.11.36 | 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 | ? | |
| 1.14.11.36 | 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 | ? | |
| 1.14.11.36 | 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 | ? | |
| 1.14.11.36 | 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 | ? | |
| 1.14.11.36 | pentalenolactone D + 2 2-oxoglutarate | - |
Streptomyces exfoliatus | pentalenolactone F + 2 succinate + 2 CO2 + H2O | - |
? | |
| 1.14.11.36 | pentalenolactone D + 2 2-oxoglutarate | - |
Streptomyces arenae | pentalenolactone F + 2 succinate + 2 CO2 + H2O | - |
? | |
| 1.14.11.36 | pentalenolactone D + 2 2-oxoglutarate | - |
Streptomyces exfoliatus UC5319 | pentalenolactone F + 2 succinate + 2 CO2 + H2O | - |
? | |
| 1.14.11.36 | pentalenolactone D + 2 2-oxoglutarate | - |
Streptomyces arenae TU469 | pentalenolactone F + 2 succinate + 2 CO2 + H2O | - |
? | |
| 1.14.13.170 | 1-deoxy-11-oxopentalenic acid + NADPH + H+ + O2 | - |
Streptomyces exfoliatus | pentalenolactone D + NADP+ + H2O | - |
ir | |
| 1.14.13.170 | 1-deoxy-11-oxopentalenic acid + NADPH + H+ + O2 | - |
Streptomyces arenae | pentalenolactone D + NADP+ + H2O | - |
ir | |
| 1.14.13.170 | 1-deoxy-11-oxopentalenic acid + NADPH + H+ + O2 | - |
Streptomyces arenae TU46 | pentalenolactone D + NADP+ + H2O | - |
ir | |
| 1.14.13.170 | 1-deoxy-11-oxopentalenic acid + NADPH + H+ + O2 | - |
Streptomyces exfoliatus UC5319 | pentalenolactone D + NADP+ + H2O | - |
ir | |
| 1.14.13.170 | 1-deoxy-11-oxopentalenic acid + NADPH + H+ + O2 | - |
Streptomyces arenae TUE469 | pentalenolactone D + NADP+ + H2O | - |
ir | |
| 1.14.13.171 | 1-deoxy-11-oxopentalenate + NADPH + H+ + O2 | - |
Streptomyces exfoliatus | neopentalenolactone D + NADP+ + H2O | - |
? | |
| 1.14.13.171 | 1-deoxy-11-oxopentalenate + NADPH + H+ + O2 | - |
Streptomyces avermitilis | neopentalenolactone D + NADP+ + H2O | - |
? | |
| 1.14.13.171 | 1-deoxy-11-oxopentalenate + NADPH + H+ + O2 | - |
Streptomyces arenae | neopentalenolactone D + NADP+ + H2O | - |
? | |
| 1.14.13.171 | 1-deoxy-11-oxopentalenate + NADPH + H+ + O2 | - |
Streptomyces arenae TU46 | neopentalenolactone D + NADP+ + H2O | - |
? | |
| 1.14.13.171 | 1-deoxy-11-oxopentalenate + NADPH + H+ + O2 | - |
Streptomyces exfoliatus UC5319 | neopentalenolactone D + NADP+ + H2O | - |
? | |
| 1.14.13.171 | 1-deoxy-11-oxopentalenate + NADPH + H+ + O2 | - |
Streptomyces arenae TUE469 | neopentalenolactone D + NADP+ + H2O | - |
? | |
Subunits
| EC Number | Subunits | Comment | Organism |
|---|---|---|---|
| 1.14.13.170 | ? | x * 66915, His6-tagged enzyme, MALDI-TOF mass spectrometry | Streptomyces arenae |
| 1.14.13.170 | ? | x * 67480, His6-tagged enzyme, MALDI-TOF mass spectrometry | Streptomyces exfoliatus |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.14.11.36 | penD | - |
Streptomyces exfoliatus |
| 1.14.11.36 | penD | - |
Streptomyces arenae |
| 1.14.13.170 | Baeyer-Villiger monooxygenase | - |
Streptomyces exfoliatus |
| 1.14.13.170 | Baeyer-Villiger monooxygenase | - |
Streptomyces arenae |
| 1.14.13.170 | penE | - |
Streptomyces exfoliatus |
| 1.14.13.170 | pntE | - |
Streptomyces arenae |
| 1.14.13.171 | penE | - |
Streptomyces exfoliatus |
| 1.14.13.171 | pntE | - |
Streptomyces arenae |
| 1.14.13.171 | ptlE | - |
Streptomyces avermitilis |
Cofactor
| EC Number | Cofactor | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.14.13.170 | FAD | the enzyme contains one bound FAD molecule | Streptomyces exfoliatus | |
| 1.14.13.170 | FAD | the enzyme contains one bound FAD molecule | Streptomyces arenae | |
| 1.14.13.171 | FAD | - |
Streptomyces exfoliatus | |
| 1.14.13.171 | FAD | - |
Streptomyces avermitilis | |
| 1.14.13.171 | FAD | - |
Streptomyces arenae | |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 1.14.11.36 | 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 |
| 1.14.11.36 | 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 |
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