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Literature summary extracted from

  • de Gonzalo, G.; Torres Pazmino, D.E.; Ottolina, G.; Fraaije, M.W.; Carrea, G.
    4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB as an oxidative biocatalyst in the synthesis of optically active sulfoxides (2006), Tetrahedron Asymmetry, 17, 130-135.
No PubMed abstract available

Application

EC Number Application Comment Organism
1.14.13.84 synthesis the enzyme can be useful in the highly enantioselective in the synthesis of chiral phenyl and benzyl sulfoxides 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
-
 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 (4-hydroxyphenyl)ethan-1-one + NADPH + O2 Pseudomonas fluorescens ACB
-
 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.13.84 Pseudomonas fluorescens
-
 gene hapE
-
1.14.13.84 Pseudomonas fluorescens ACB
-
 gene hapE
-

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
-
 Pseudomonas fluorescens 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 (4-hydroxyphenyl)ethan-1-one + NADPH + O2
-
 Pseudomonas fluorescens ACB 4-hydroxyphenyl acetate + NADP+ + H2O
-
 ?
1.14.13.84 2-chloro-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 2-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
 ?
1.14.13.84 2-chloro-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens ACB 2-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
 ?
1.14.13.84 2-chloro-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 2-chlorophenyl methyl (S)-sulfoxide + NADP+ + H2O 96% enantiomeric excess ?
1.14.13.84 2-chloroethyl phenyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens 2-chloroethyl phenyl (S)-sulfoxide + NADP+ + H2O 81% enantiomeric excess ?
1.14.13.84 3-chloro-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 3-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
 ?
1.14.13.84 3-chloro-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens ACB 3-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
 ?
1.14.13.84 3-chloro-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 3-chlorophenyl methyl (S)-sulfoxide + NADP+ + H2O 99% enantiomeric excess ?
1.14.13.84 4-amino-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-aminophenyl methyl sulfoxide + NADP+ + H2O
-
 ?
1.14.13.84 4-amino-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens ACB 4-aminophenyl methyl sulfoxide + NADP+ + H2O
-
 ?
1.14.13.84 4-amino-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-[(S)-methylsulfinyl]aniline + NADP+ + H2O 99% enantiomeric excess ?
1.14.13.84 4-chloro-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
 ?
1.14.13.84 4-chloro-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-chlorophenyl methyl (S)-sulfoxide + NADP+ + H2O 96% enantiomeric excess ?
1.14.13.84 4-cyano-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-cyanophenyl methyl sulfoxide + NADP+ + H2O
-
 ?
1.14.13.84 4-cyano-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-[(S)-methylsulfinyl]benzonitrile + NADP+ + H2O 96% enantiomeric excess ?
1.14.13.84 4-methoxy-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-methoxyphenyl methyl sulfoxide + NADP+ + H2O
-
 ?
1.14.13.84 4-methoxy-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-methoxyphenyl methyl (S)-sulfoxide + NADP+ + H2O 99% enantiomeric excess ?
1.14.13.84 4-methyl-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-methylphenyl methyl sulfoxide + NADP+ + H2O
-
 ?
1.14.13.84 4-methyl-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens methyl 4-methylphenyl (S)-sulfoxide + NADP+ + H2O 99% enantiomeric excess ?
1.14.13.84 4-nitro-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens 4-nitrophenyl methyl sulfoxide + NADP+ + H2O
-
 ?
1.14.13.84 4-nitro-thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens methyl 4-nitrophenyl (S)-sulfoxide + NADP+ + H2O 87% enantiomeric excess ?
1.14.13.84 benzyl 1-methylethyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens benzyl 1-methylethyl (R)-sulfoxide + NADP+ + H2O 82% enantiomeric excess ?
1.14.13.84 benzyl butyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens benzyl butyl (R)-sulfoxide + NADP+ + H2O 77% enantiomeric excess ?
1.14.13.84 benzyl ethyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens benzyl ethyl (S)-sulfoxide + NADP+ + H2O 81% enantiomeric excess ?
1.14.13.84 benzyl methyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens benzyl methyl (S)-sulfoxide + NADP+ + H2O 85% enantiomeric excess ?
1.14.13.84 benzyl propyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens benzyl propyl (R)-sulfoxide + NADP+ + H2O 65% enantiomeric excess ?
1.14.13.84 butyl phenyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens butyl phenyl (S)-sulfoxide + NADP+ + H2O 71% enantiomeric excess ?
1.14.13.84 chloromethyl phenyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens chloromethyl phenyl (R)-sulfoxide + NADP+ + H2O 76% enantiomeric excess ?
1.14.13.84 cyclopropyl phenyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens cyclopropyl phenyl (S)-sulfoxide + NADP+ + H2O 97% enantiomeric excess ?
1.14.13.84 ethenyl phenyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens ethenyl phenyl (S)-sulfoxide + NADP+ + H2O 98% enantiomeric excess ?
1.14.13.84 ethyl phenyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens ethyl phenyl (S)-sulfoxide + NADP+ + H2O 99% enantiomeric excess ?
1.14.13.84 methyl (phenylsulfanyl)methyl ether + NADPH + H+ + O2
-
 Pseudomonas fluorescens methoxymethyl phenyl (R)-sulfoxide + NADP+ + H2O 98% enantiomeric excess ?
1.14.13.84 methyl 2-phenylethyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens methyl 2-phenylethyl (R)-sulfoxide + NADP+ + H2O 51% enantiomeric excess ?
1.14.13.84 methyl 3-phenylpropyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens methyl 3-phenylpropyl (R)-sulfoxide + NADP+ + H2O 57% enantiomeric excess ?
1.14.13.84 methyl naphthalen-2-yl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens methyl naphthalen-2-yl (S)-sulfoxide + NADP+ + H2O 95% enantiomeric excess ?
1.14.13.84 additional information the recombinant enzyme is highly enantioselective in the synthesis of chiral phenyl and benzyl sulfoxides, oxidation of aromatic sulfides, substrate specificity and enantioselectivity, overview Pseudomonas fluorescens ?
-
 ?
1.14.13.84 additional information the recombinant enzyme is highly enantioselective in the synthesis of chiral phenyl and benzyl sulfoxides, oxidation of aromatic sulfides, substrate specificity and enantioselectivity, overview Pseudomonas fluorescens ACB ?
-
 ?
1.14.13.84 phenyl prop-2-en-1-yl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens phenyl prop-2-en-1-yl (S)-sulfoxide + NADP+ + H2O 98% enantiomeric excess ?
1.14.13.84 phenyl propyl sulfide + NADPH + H+ + O2
-
 Pseudomonas fluorescens phenyl propyl (S)-sulfoxide + NADP+ + H2O 97% enantiomeric excess ?
1.14.13.84 thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens methyl phenyl sulfoxide + NADP+ + H2O
-
 ?
1.14.13.84 thioanisole + NADPH + H+ + O2
-
 Pseudomonas fluorescens methyl phenyl (S)-sulfoxide + NADP+ + H2O 99% enantiomeric excess ?

Synonyms

EC Number Synonyms Comment Organism
1.14.13.84 HAPMO
-
 Pseudomonas fluorescens
1.14.13.84 More the enzyme is a Baeyer–Villiger monooxygenase Pseudomonas fluorescens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.13.84 25
-
 assay at Pseudomonas fluorescens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.13.84 9
-
 assay at Pseudomonas fluorescens

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.13.84 FAD flavoenzyme Pseudomonas fluorescens
1.14.13.84 NADPH dependent on Pseudomonas fluorescens