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Literature summary for 1.14.13.84 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

Application Comment Organism
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)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(4-hydroxyphenyl)ethan-1-one + NADPH + O2 Pseudomonas fluorescens
-
4-hydroxyphenyl acetate + NADP+ + H2O
-
?
(4-hydroxyphenyl)ethan-1-one + NADPH + O2 Pseudomonas fluorescens ACB
-
4-hydroxyphenyl acetate + NADP+ + H2O
-
?

Organism

Organism UniProt Comment Textmining
Pseudomonas fluorescens
-
gene hapE
-
Pseudomonas fluorescens ACB
-
gene hapE
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
-
Pseudomonas fluorescens 4-hydroxyphenyl acetate + NADP+ + H2O
-
?
(4-hydroxyphenyl)ethan-1-one + NADPH + O2
-
Pseudomonas fluorescens ACB 4-hydroxyphenyl acetate + NADP+ + H2O
-
?
2-chloro-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 2-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
?
2-chloro-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens ACB 2-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
?
2-chloro-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 2-chlorophenyl methyl (S)-sulfoxide + NADP+ + H2O 96% enantiomeric excess ?
2-chloroethyl phenyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens 2-chloroethyl phenyl (S)-sulfoxide + NADP+ + H2O 81% enantiomeric excess ?
3-chloro-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 3-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
?
3-chloro-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens ACB 3-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
?
3-chloro-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 3-chlorophenyl methyl (S)-sulfoxide + NADP+ + H2O 99% enantiomeric excess ?
4-amino-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-aminophenyl methyl sulfoxide + NADP+ + H2O
-
?
4-amino-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens ACB 4-aminophenyl methyl sulfoxide + NADP+ + H2O
-
?
4-amino-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-[(S)-methylsulfinyl]aniline + NADP+ + H2O 99% enantiomeric excess ?
4-chloro-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-chlorophenyl methyl sulfoxide + NADP+ + H2O
-
?
4-chloro-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-chlorophenyl methyl (S)-sulfoxide + NADP+ + H2O 96% enantiomeric excess ?
4-cyano-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-cyanophenyl methyl sulfoxide + NADP+ + H2O
-
?
4-cyano-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-[(S)-methylsulfinyl]benzonitrile + NADP+ + H2O 96% enantiomeric excess ?
4-methoxy-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-methoxyphenyl methyl sulfoxide + NADP+ + H2O
-
?
4-methoxy-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-methoxyphenyl methyl (S)-sulfoxide + NADP+ + H2O 99% enantiomeric excess ?
4-methyl-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-methylphenyl methyl sulfoxide + NADP+ + H2O
-
?
4-methyl-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens methyl 4-methylphenyl (S)-sulfoxide + NADP+ + H2O 99% enantiomeric excess ?
4-nitro-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens 4-nitrophenyl methyl sulfoxide + NADP+ + H2O
-
?
4-nitro-thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens methyl 4-nitrophenyl (S)-sulfoxide + NADP+ + H2O 87% enantiomeric excess ?
benzyl 1-methylethyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens benzyl 1-methylethyl (R)-sulfoxide + NADP+ + H2O 82% enantiomeric excess ?
benzyl butyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens benzyl butyl (R)-sulfoxide + NADP+ + H2O 77% enantiomeric excess ?
benzyl ethyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens benzyl ethyl (S)-sulfoxide + NADP+ + H2O 81% enantiomeric excess ?
benzyl methyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens benzyl methyl (S)-sulfoxide + NADP+ + H2O 85% enantiomeric excess ?
benzyl propyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens benzyl propyl (R)-sulfoxide + NADP+ + H2O 65% enantiomeric excess ?
butyl phenyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens butyl phenyl (S)-sulfoxide + NADP+ + H2O 71% enantiomeric excess ?
chloromethyl phenyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens chloromethyl phenyl (R)-sulfoxide + NADP+ + H2O 76% enantiomeric excess ?
cyclopropyl phenyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens cyclopropyl phenyl (S)-sulfoxide + NADP+ + H2O 97% enantiomeric excess ?
ethenyl phenyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens ethenyl phenyl (S)-sulfoxide + NADP+ + H2O 98% enantiomeric excess ?
ethyl phenyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens ethyl phenyl (S)-sulfoxide + NADP+ + H2O 99% enantiomeric excess ?
methyl (phenylsulfanyl)methyl ether + NADPH + H+ + O2
-
Pseudomonas fluorescens methoxymethyl phenyl (R)-sulfoxide + NADP+ + H2O 98% enantiomeric excess ?
methyl 2-phenylethyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens methyl 2-phenylethyl (R)-sulfoxide + NADP+ + H2O 51% enantiomeric excess ?
methyl 3-phenylpropyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens methyl 3-phenylpropyl (R)-sulfoxide + NADP+ + H2O 57% enantiomeric excess ?
methyl naphthalen-2-yl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens methyl naphthalen-2-yl (S)-sulfoxide + NADP+ + H2O 95% enantiomeric excess ?
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 ?
-
?
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 ?
-
?
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 ?
phenyl propyl sulfide + NADPH + H+ + O2
-
Pseudomonas fluorescens phenyl propyl (S)-sulfoxide + NADP+ + H2O 97% enantiomeric excess ?
thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens methyl phenyl sulfoxide + NADP+ + H2O
-
?
thioanisole + NADPH + H+ + O2
-
Pseudomonas fluorescens methyl phenyl (S)-sulfoxide + NADP+ + H2O 99% enantiomeric excess ?

Synonyms

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

Temperature Optimum [°C]

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

pH Optimum

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

Cofactor

Cofactor Comment Organism Structure
FAD flavoenzyme Pseudomonas fluorescens
NADPH dependent on Pseudomonas fluorescens