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Literature summary extracted from

  • Rioz-Martinez, A.; De Gonzal, D.G.; Torres Pazmino, D.; Fraaije, M.; Gotor, V.
    Enzymatic Baeyer-Villiger oxidation of Benzo-Fused ketones: Formation of regiocomplementary lactones (2009), Eur. J. Org. Chem., 15, 2526-2532.
No PubMed abstract available

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.13.84 overexpression of recombinant enzyme in Escherichia coli BL21(DE3)pLysS Pseudomonas fluorescens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.13.84 (4-hydroxyphenyl)ethan-1-one + NADPH + O2 Pseudomonas fluorescens 1 unit enzyme oxidizes 1 micromol substrate to product per minute at pH 9.0, 25°C in the presence of NADPH 4-hydroxyphenyl acetate + NADP+ + H2O
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 ?
1.14.13.84 (4-hydroxyphenyl)ethan-1-one + NADPH + O2 Pseudomonas fluorescens ACB 1 unit enzyme oxidizes 1 micromol substrate to product per minute at pH 9.0, 25°C in the presence of NADPH 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.13.84 Pseudomonas fluorescens Q93TJ5 ACB
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1.14.13.84 Pseudomonas fluorescens ACB Q93TJ5 ACB
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Purification (Commentary)

EC Number Purification (Comment) Organism
1.14.13.84 recombinant enzyme Pseudomonas fluorescens

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.13.84 (4-hydroxyphenyl)ethan-1-one + NADPH + O2 1 unit enzyme oxidizes 1 micromol substrate to product per minute at pH 9.0, 25°C in the presence of NADPH Pseudomonas fluorescens 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 (4-hydroxyphenyl)ethan-1-one + NADPH + O2 1 unit enzyme oxidizes 1 micromol substrate to product per minute at pH 9.0, 25°C in the presence of NADPH Pseudomonas fluorescens ACB 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 1-indanone + NADPH + H+ + O2 50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH Pseudomonas fluorescens 3,4-dihydrocoumarin + NADP+ + H2O after 72 h 26% conversion without cosolvent, with 5% 2-octanole 39% conversion, with 5% hexane 44% conversion, conversion with 5% hexane at pH 8.0 is 39%, at pH 9.0 44%, at pH 10.0 47%, at pH 10.5 21% ?
1.14.13.84 1-indanone + NADPH + H+ + O2 50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH Pseudomonas fluorescens ACB 3,4-dihydrocoumarin + NADP+ + H2O after 72 h 26% conversion without cosolvent, with 5% 2-octanole 39% conversion, with 5% hexane 44% conversion, conversion with 5% hexane at pH 8.0 is 39%, at pH 9.0 44%, at pH 10.0 47%, at pH 10.5 21% ?
1.14.13.84 1-tetralone + NADPH + H+ + O2 50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH Pseudomonas fluorescens 4,5-dihydro-1-benzoxepin-2(3H)-one + NADP+ + H2O after 96 h only 5% of the expected product conversion without cosolvent, with 5% tBuOMe 7% conversion, with 5% toluene 26% conversion, with 5% 2-octanol 25% conversion, with 5% hexane 15% conversion ?
1.14.13.84 1-tetralone + NADPH + H+ + O2 50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH Pseudomonas fluorescens ACB 4,5-dihydro-1-benzoxepin-2(3H)-one + NADP+ + H2O after 96 h only 5% of the expected product conversion without cosolvent, with 5% tBuOMe 7% conversion, with 5% toluene 26% conversion, with 5% 2-octanol 25% conversion, with 5% hexane 15% conversion ?
1.14.13.84 2-indanone + NADPH + H+ + O2 50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH Pseudomonas fluorescens 3-isochromanone + NADP+ + H2O after 72 h no product without cosolvent, only with 5% hexane or 5% CH2Cl2 10% conversion ?
1.14.13.84 2-indanone + NADPH + H+ + O2 50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH Pseudomonas fluorescens ACB 3-isochromanone + NADP+ + H2O after 72 h no product without cosolvent, only with 5% hexane or 5% CH2Cl2 10% conversion ?
1.14.13.84 5-bromo-1-indanone + NADPH + H+ + O2 50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH Pseudomonas fluorescens 5-bromo-3,4-dihydrochromen-2-one + NADP+ + H2O after 72 h lower activity than towards chlorine derivative, with 5% hexane 52% conversion ?
1.14.13.84 5-chloro-1-indanone + NADPH + H+ + O2 50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH Pseudomonas fluorescens 5-chloro-3,4-dihydrochromen-2-one + NADP+ + H2O after 72 h lower conversion without cosolvent than with 5% hexane (87% conversion) ?
1.14.13.84 5-methoxy-1-indanone + NADPH + H+ + O2 50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH Pseudomonas fluorescens 5-methoxy-3,4-dihydrochromen-2-one + NADP+ + H2O after 72 h with 5% hexane 32% conversion ?
1.14.13.84 6-chloro-1-indanone + NADPH + H+ + O2 50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH Pseudomonas fluorescens 7-chloro-3,4-dihydrochromen-2-one + NADP+ + H2O after 72 h higher conversion without cosolvent than with 5% hexane (56% conversion) ?
1.14.13.84 6-methoxy-1-indanone + NADPH + H+ + O2 50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH Pseudomonas fluorescens 6-methoxy-3,4-dihydrochromen-2-one + NADP+ + H2O after 72 h with 5% hexane 32% conversion ?
1.14.13.84 benzocyclobutanone + NADPH + H+ + O2 50 mM Tris-HCl, pH 9.0, 20°C, auxiliary enzymatic system (glucose-6-phosphate with glucose-6-phosphate dehydrogenase) is used to regenerate NADPH Pseudomonas fluorescens coumaranone + NADP+ + H2O after 72 h 87% conversion, with 5% hexane 93% conversion ?
1.14.13.84 additional information no reaction with 2-tetralone or 4-methoxy-1-indanone as substrate, no effect of changed conditions (pH, temperature, organic cosolvents) Pseudomonas fluorescens ?
-
 ?
1.14.13.84 additional information no reaction with 2-tetralone or 4-methoxy-1-indanone as substrate, no effect of changed conditions (pH, temperature, organic cosolvents) Pseudomonas fluorescens ACB ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.13.84 4-hydroxyacetophenone monooxygenase
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 Pseudomonas fluorescens
1.14.13.84 Baeyer-Villiger monooxygenase
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 Pseudomonas fluorescens
1.14.13.84 HAPMO
-
 Pseudomonas fluorescens

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.13.84 NADPH
-
 Pseudomonas fluorescens