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- Biotransformation of organic sulfides. Predictive active site models for sulfoxidation catalyzed by 2,5-diketocamphane 1,2-monooxygenase and 3,6-diketocamphane 1,6-monooxygenase, enantiocomplementary enzymes from Pseudomonas putida NCIMB 10007 (1998), Tetrahedron, 9, 1899-1916.
No PubMed abstract available
Application
| EC Number | Application | Comment | Organism |
|---|---|---|---|
| 1.14.14.108 | synthesis | production of useful chiral synthons for chemoenzymatic synthesis | Pseudomonas putida |
| 1.14.14.155 | synthesis | production of useful chiral synthons for chemoenzymatic synthesis | Pseudomonas putida |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.14.108 | (+)-bornane-2,5-dione + FMNH2 + O2 | Pseudomonas putida | inducible by growth on racemic camphor | ? | - |
? |  |
| 1.14.14.108 | additional information | Pseudomonas putida | catalyzes stereoselective electrophilic biooxidation of a wide range of prochiral organic sulfoxides to the corresponding chiral sulfoxides as well as the nucleophilic biooxidation of ketones to lactones with different enantio- and stereoselectivity, overview | ? | - |
? | |
| 1.14.14.108 | additional information | Pseudomonas putida NCIMB 10007 | catalyzes stereoselective electrophilic biooxidation of a wide range of prochiral organic sulfoxides to the corresponding chiral sulfoxides as well as the nucleophilic biooxidation of ketones to lactones with different enantio- and stereoselectivity, overview | ? | - |
? | |
| 1.14.14.155 | (-)-bornane-2,5-dione + FMNH2 + O2 | Pseudomonas putida | inducible by growth on racemic camphor | ? | - |
? | |
| 1.14.14.155 | additional information | Pseudomonas putida | catalyzes stereoselective electrophilic biooxidation of a wide range of prochiral organic sulfoxides to the corresponding chiral sulfoxides as well as the nucleophilic biooxidation of ketones to lactones with different enantio- and stereoselectivity, overview | ? | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.14.14.108 | Pseudomonas putida | - |
- |
- |
| 1.14.14.108 | Pseudomonas putida | - |
2 isozymes termed 2,5-diketocamphane-1,2-monooxygenase and 3,6-diketocamphane-1,6-monooxygenase | - |
| 1.14.14.108 | Pseudomonas putida NCIMB 10007 | - |
- |
- |
| 1.14.14.155 | Pseudomonas putida | - |
- |
- |
| 1.14.14.155 | Pseudomonas putida | - |
2 isozymes termed 2,5-diketocamphane-1,2-monooxygenase and 3,6-diketocamphane-1,6-monooxygenase | - |
| 1.14.14.155 | Pseudomonas putida NCIMB 10007 | - |
- |
- |
Purification (Commentary)
| EC Number | Purification (Comment) | Organism |
|---|---|---|
| 1.14.14.108 | - |
Pseudomonas putida |
| 1.14.14.155 | - |
Pseudomonas putida |
Reaction
| EC Number | Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|---|
| 1.14.14.108 | (+)-bornane-2,5-dione + FMNH2 + O2 = (+)-5-oxo-1,2-campholide + FMN + H2O | mechanism | Pseudomonas putida | |
| 1.14.14.108 | (+)-bornane-2,5-dione + FMNH2 + O2 = (+)-5-oxo-1,2-campholide + FMN + H2O | catalysis of 2 mechanistically different types of biochemical reactions within the confines of the same active site | Pseudomonas putida | |
| 1.14.14.108 | (+)-bornane-2,5-dione + FMNH2 + O2 = (+)-5-oxo-1,2-campholide + FMN + H2O | higher activity in lactonization of ketones than in oxidation of sulfides to the corresponding sulfoxides | Pseudomonas putida | |
| 1.14.14.108 | (+)-bornane-2,5-dione + FMNH2 + O2 = (+)-5-oxo-1,2-campholide + FMN + H2O | belongs to group of Bayer-Villiger monooxygenases of the NADH plus FMN-dependent type 2 enzymes | Pseudomonas putida | |
| 1.14.14.108 | (+)-bornane-2,5-dione + FMNH2 + O2 = (+)-5-oxo-1,2-campholide + FMN + H2O | cubic space active site model, topography | Pseudomonas putida | |
| 1.14.14.155 | (-)-bornane-2,5-dione + reduced rubredoxin + O2 + FMNH2 = (-)-5-oxo-1,2-campholide + FMN + H2O | mechanism | Pseudomonas putida | |
| 1.14.14.155 | (-)-bornane-2,5-dione + reduced rubredoxin + O2 + FMNH2 = (-)-5-oxo-1,2-campholide + FMN + H2O | catalysis of 2 mechanistically different types of biochemical reactions within the confines of the same active site | Pseudomonas putida | |
| 1.14.14.155 | (-)-bornane-2,5-dione + reduced rubredoxin + O2 + FMNH2 = (-)-5-oxo-1,2-campholide + FMN + H2O | belongs to group of Bayer-Villiger monooxygenases of the NADH plus FMN-dependent type 2 enzymes | Pseudomonas putida | |
| 1.14.14.155 | (-)-bornane-2,5-dione + reduced rubredoxin + O2 + FMNH2 = (-)-5-oxo-1,2-campholide + FMN + H2O | cubic space active site model, topography | Pseudomonas putida | |
| 1.14.14.155 | (-)-bornane-2,5-dione + reduced rubredoxin + O2 + FMNH2 = (-)-5-oxo-1,2-campholide + FMN + H2O | isozyme, enantiocomplementary and isofunctional isozymes 2,5-DKCMO EC 1.14.15.2 and 3,6-DKCMO EC 1.14.15.x | Pseudomonas putida | |
| 1.14.14.155 | (-)-bornane-2,5-dione + reduced rubredoxin + O2 + FMNH2 = (-)-5-oxo-1,2-campholide + FMN + H2O | higher activity in oxidation of sulfides to the corresponding sulfoxides than in lactonization of ketones | Pseudomonas putida |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.14.108 | (+)-bornane-2,5-dione + FMNH2 + O2 | i.e. 2,5-diketocamphane | Pseudomonas putida | 3,4,4-trimethyl-5-carboxy-methyl-DELTA2-cyclopentenone + FMN + H2O | - |
? | |
| 1.14.14.108 | (+)-bornane-2,5-dione + FMNH2 + O2 | i.e. 2,5-diketocamphane | Pseudomonas putida NCIMB 10007 | 3,4,4-trimethyl-5-carboxy-methyl-DELTA2-cyclopentenone + FMN + H2O | - |
? | |
| 1.14.14.108 | (+)-bornane-2,5-dione + FMNH2 + O2 | inducible by growth on racemic camphor | Pseudomonas putida | ? | - |
? | |
| 1.14.14.108 | (+)-bornanone + FMNH2 + O2 | (+)-camphor | Pseudomonas putida | 1,2-campholide + FMN + H2O | - |
? | |
| 1.14.14.108 | (+)-bornanone + FMNH2 + O2 | (+)-camphor | Pseudomonas putida NCIMB 10007 | 1,2-campholide + FMN + H2O | - |
? | |
| 1.14.14.108 | additional information | enzyme is associated with a NADH oxidase | Pseudomonas putida | ? | - |
? | |
| 1.14.14.108 | additional information | rubredoxin not mentioned | Pseudomonas putida | ? | - |
? | |
| 1.14.14.108 | additional information | catalyzes stereoselective electrophilic biooxidation of a wide range of prochiral organic sulfoxides to the corresponding chiral sulfoxides as well as the nucleophilic biooxidation of ketones to lactones with different enantio- and stereoselectivity, overview | Pseudomonas putida | ? | - |
? | |
| 1.14.14.108 | additional information | enzyme is associated with a NADH oxidase | Pseudomonas putida NCIMB 10007 | ? | - |
? | |
| 1.14.14.108 | additional information | rubredoxin not mentioned | Pseudomonas putida NCIMB 10007 | ? | - |
? | |
| 1.14.14.108 | additional information | catalyzes stereoselective electrophilic biooxidation of a wide range of prochiral organic sulfoxides to the corresponding chiral sulfoxides as well as the nucleophilic biooxidation of ketones to lactones with different enantio- and stereoselectivity, overview | Pseudomonas putida NCIMB 10007 | ? | - |
? | |
| 1.14.14.155 | (-)-bornane-2,5-dione + FMNH2 + O2 | 6-dione i.e. 3,6-diketocamphane | Pseudomonas putida | 1,8,8-trimethyl-2-oxabicyclo[3.2.1]octane-3,6-dione + FMN + H2O | - |
? | |
| 1.14.14.155 | (-)-bornane-2,5-dione + FMNH2 + O2 | inducible by growth on racemic camphor | Pseudomonas putida | ? | - |
? | |
| 1.14.14.155 | (-)-bornanone + FMNH2 + O2 | i.e. (-)-camphor | Pseudomonas putida | ? | - |
? | |
| 1.14.14.155 | additional information | enzyme is associated with a NADH oxidase | Pseudomonas putida | ? | - |
? | |
| 1.14.14.155 | additional information | rubredoxin not mentioned | Pseudomonas putida | ? | - |
? | |
| 1.14.14.155 | additional information | catalyzes stereoselective electrophilic biooxidation of a wide range of prochiral organic sulfoxides to the corresponding chiral sulfoxides as well as the nucleophilic biooxidation of ketones to lactones with different enantio- and stereoselectivity, overview | Pseudomonas putida | ? | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 1.14.14.108 | 2,5-diketocamphane 1,2-monooxygenase | - |
Pseudomonas putida |
| 1.14.14.108 | 2,5-DKCMO | - |
Pseudomonas putida |
| 1.14.14.108 | 3,6-diketocamphane 1,6-monooxygenase | isoform, which is probably a different enzyme, i.e. 3,6-DKCMO | Pseudomonas putida |
| 1.14.14.108 | 3,6-diketocamphane 1,6-monooxygenase | isoenzyme, enantiocomplementary and isofunctional isozymes 2,5-DKCMO EC 1.14.15.2 and 3,6-DKCMO EC 1.14.15.x | Pseudomonas putida |
| 1.14.14.155 | 3,6-diketocamphane 1,6-monooxygenase | isozyme, enantiocomplementary and isofunctional isozymes 2,5-DKCMO EC 1.14.15.2 and 3,6-DKCMO EC 1.14.15.x | Pseudomonas putida |
| 1.14.14.155 | 3,6-diketocamphane 1,6-monooxygenase | i.e. 3,6-DKCMO | Pseudomonas putida |
| 1.14.14.155 | 3,6-diketocamphane 1,6-monooxygenase | isoform, which is probably a different enzyme | Pseudomonas putida |
| 1.14.14.155 | 3,6-diketocamphane-monooxygenase | - |
Pseudomonas putida |
Cofactor
| EC Number | Cofactor | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.14.14.108 | FMN | - |
Pseudomonas putida | |
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