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Literature summary for 1.14.14.108 extracted from

  • Beecher, J.; Willetts, A.
    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
Search for more literature for 1.14.14.108

Application

Application Comment Organism
synthesis production of useful chiral synthons for chemoenzymatic synthesis Pseudomonas putida

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(+)-bornane-2,5-dione + FMNH2 + O2 Pseudomonas putida inducible by growth on racemic camphor ?
-
 ?
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 ?
-
 ?
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 ?
-
 ?

Organism

Organism UniProt Comment Textmining
Pseudomonas putida
-
-
-
Pseudomonas putida
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 2 isozymes termed 2,5-diketocamphane-1,2-monooxygenase and 3,6-diketocamphane-1,6-monooxygenase
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Pseudomonas putida NCIMB 10007
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-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Pseudomonas putida

Reaction

Reaction Comment Organism Reaction ID
(+)-bornane-2,5-dione + FMNH2 + O2 = (+)-5-oxo-1,2-campholide + FMN + H2O mechanism Pseudomonas putida
a
(+)-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
a
(+)-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
a
(+)-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
a
(+)-bornane-2,5-dione + FMNH2 + O2 = (+)-5-oxo-1,2-campholide + FMN + H2O cubic space active site model, topography Pseudomonas putida
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(+)-bornane-2,5-dione + FMNH2 + O2 i.e. 2,5-diketocamphane Pseudomonas putida 3,4,4-trimethyl-5-carboxy-methyl-DELTA2-cyclopentenone + FMN + H2O
-
 ?
(+)-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
-
 ?
(+)-bornane-2,5-dione + FMNH2 + O2 inducible by growth on racemic camphor Pseudomonas putida ?
-
 ?
(+)-bornanone + FMNH2 + O2 (+)-camphor Pseudomonas putida 1,2-campholide + FMN + H2O
-
 ?
(+)-bornanone + FMNH2 + O2 (+)-camphor Pseudomonas putida NCIMB 10007 1,2-campholide + FMN + H2O
-
 ?
additional information enzyme is associated with a NADH oxidase Pseudomonas putida ?
-
 ?
additional information rubredoxin not mentioned Pseudomonas putida ?
-
 ?
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 ?
-
 ?
additional information enzyme is associated with a NADH oxidase Pseudomonas putida NCIMB 10007 ?
-
 ?
additional information rubredoxin not mentioned Pseudomonas putida NCIMB 10007 ?
-
 ?
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 ?
-
 ?

Synonyms

Synonyms Comment Organism
2,5-diketocamphane 1,2-monooxygenase
-
 Pseudomonas putida
2,5-DKCMO
-
 Pseudomonas putida
3,6-diketocamphane 1,6-monooxygenase isoform, which is probably a different enzyme, i.e. 3,6-DKCMO Pseudomonas putida
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

Cofactor

Cofactor Comment Organism Structure
FMN
-
 Pseudomonas putida