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Literature summary extracted from
- CH-activating oxidative hydroxylation of 1-tetralones and related compounds with high regio- and stereoselectivity (2014), Chem. Commun. (Camb.), 50, 14310-14313 .
Application
| EC Number | Application | Comment | Organism |
|---|---|---|---|
| 1.14.14.1 | synthesis | P450-BM3 enzyme mutants are ueful for CH-activating oxidative hydroxylation of readily available 1-tetralone derivatives with high degrees of regio- and stereoselectivity, e.g. oxidative hydroxylation of indane and tetralin, an approach which is currently not possible using chiral synthetic CH-activating transition metal catalysts | Priestia megaterium |
Protein Variants
| EC Number | Protein Variants | Comment | Organism |
|---|---|---|---|
| 1.14.14.1 | A328F | site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme | Priestia megaterium |
| 1.14.14.1 | A328K | site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme | Priestia megaterium |
| 1.14.14.1 | A328R | site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme | Priestia megaterium |
| 1.14.14.1 | A328Y | site-directed mutagenesis, the mutant shows altered enantioselectivity compared to the wild-type enzyme | Priestia megaterium |
| 1.14.14.1 | additional information | mutants of enzyme P450-BM3 evolved by directed evolution are excellent catalysts in the CH-activating oxidative hydroxylation of 1-tetralone derivatives and of indanone, with unusually high regio- and enantioselectivity | Priestia megaterium |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.14.1 | indane + [reduced NADPH-hemoprotein reductase] + O2 | Priestia megaterium | - |
(S)-3-hydroxy-indane + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? |  |
| 1.14.14.1 | indane + [reduced NADPH-hemoprotein reductase] + O2 | Priestia megaterium ATCC 14581 | - |
(S)-3-hydroxy-indane + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.1 | tetralin + [reduced NADPH-hemoprotein reductase] + O2 | Priestia megaterium | - |
(S)-4-hydroxy-tetralin + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.1 | tetralin + [reduced NADPH-hemoprotein reductase] + O2 | Priestia megaterium ATCC 14581 | - |
(S)-4-hydroxy-tetralin + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.14.14.1 | Priestia megaterium | P14779 | - |
- |
| 1.14.14.1 | Priestia megaterium ATCC 14581 | P14779 | - |
- |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.14.1 | 1-indanone + [reduced NADPH-hemoprotein reductase] + O2 | - |
Priestia megaterium | (S)-3-hydroxy-1-indanone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.1 | 1-indanone + [reduced NADPH-hemoprotein reductase] + O2 | - |
Priestia megaterium ATCC 14581 | (S)-3-hydroxy-1-indanone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.1 | 1-tetralone + [reduced NADPH-hemoprotein reductase] + O2 | - |
Priestia megaterium | (S)-4-hydroxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.1 | 1-tetralone + [reduced NADPH-hemoprotein reductase] + O2 | - |
Priestia megaterium ATCC 14581 | (S)-4-hydroxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.1 | 6-methoxy-1-tetralone + [reduced NADPH-hemoprotein reductase] + O2 | - |
Priestia megaterium | (S)-4-hydroxy-6-methoxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.1 | 7-methoxy-1-tetralone + [reduced NADPH-hemoprotein reductase] + O2 | - |
Priestia megaterium | (S)-4-hydroxy-7-methoxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.1 | 7-methoxy-1-tetralone + [reduced NADPH-hemoprotein reductase] + O2 | - |
Priestia megaterium ATCC 14581 | (S)-4-hydroxy-7-methoxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.1 | indane + [reduced NADPH-hemoprotein reductase] + O2 | - |
Priestia megaterium | (S)-3-hydroxy-indane + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.1 | indane + [reduced NADPH-hemoprotein reductase] + O2 | - |
Priestia megaterium ATCC 14581 | (S)-3-hydroxy-indane + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.1 | tetralin + [reduced NADPH-hemoprotein reductase] + O2 | - |
Priestia megaterium | (S)-4-hydroxy-tetralin + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
| 1.14.14.1 | tetralin + [reduced NADPH-hemoprotein reductase] + O2 | - |
Priestia megaterium ATCC 14581 | (S)-4-hydroxy-tetralin + [oxidized NADPH-hemoprotein reductase] + H2O | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.14.14.1 | BG04_163 | - |
Priestia megaterium |
| 1.14.14.1 | CYP102A1 | - |
Priestia megaterium |
| 1.14.14.1 | P450-BM3 | - |
Priestia megaterium |
Cofactor
| EC Number | Cofactor | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.14.14.1 | NADPH | - |
Priestia megaterium | |
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