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Literature summary extracted from

  • Rodriguez, C.; de Gonzalo, G.; Torres Pazmino, D.E.; Fraaije, M.W.; Gotor, V.
    Selective Baeyer-Villiger oxidation of racemic ketones in aqueous-organic media catalyzed by phenylacetone monooxygenase (2008), Tetrahedron Asymmetry, 19, 197-203.
No PubMed abstract available

Application

EC Number Application Comment Organism
1.14.13.92 synthesis the enzyme is useful for kinetic resolution of a set of racemic substituted 3-phenylbutan-2-ones and synthesis of enantiopure compounds, overview Thermobifida fusca

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.13.92 additional information effects of a range of solvents on the biocatalytic properties of the biocatalyst, overview Thermobifida fusca

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.13.92 phenylacetone + NADPH + H+ + O2 Thermobifida fusca
-
 benzyl acetate + NADP+ + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.13.92 Thermobifida fusca
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
1.14.13.92 phenylacetone + NADPH + H+ + O2 = benzyl acetate + NADP+ + H2O reaction mechanism and catalytic cycle, rapid binding of NADPH is followed by a transfer of the (4R)-hydride from NADPH to the FAD cofactor. The reduced PAMO is rapidly oxygenated by molecular oxygen, yielding a C4a-peroxyflavin. The peroxyflavin enzyme intermediate, possibly a Criegee intermediate or a C4a-hydroxyflavin form, reacts with phenylacetone to form benzylacetate, residue R337 is important in catalysis, overview Thermobifida fusca
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.13.92 (R)-2-acetoxyphenylacetonitrile + NADPH + H+ + O2 enantioselective reaction Thermobifida fusca ?
-
 ?
1.14.13.92 (R)-3-(4-bromophenyl)butan-2-one + NADPH + H+ + O2 enantioselective reaction Thermobifida fusca ?
-
 ?
1.14.13.92 (S)-1-(3-trifluoromethylphenyl)ethyl acetate + NADPH + H+ + O2 enantioselective reaction Thermobifida fusca ?
-
 ?
1.14.13.92 3-(3-trifluoromethylphenyl)butan-2-one + NADPH + H+ + O2 enantioselective reaction Thermobifida fusca ?
-
 ?
1.14.13.92 3-phenyl-2-butanone + NADPH + H+ + O2 enantioselective reaction Thermobifida fusca (R)-3-phenylbutan-2-one + (S)-1-phenyethyl acetate
-
 ?
1.14.13.92 alpha-acetylphenylacetonitrile + NADPH + H+ + O2 enantioselective reaction Thermobifida fusca (R)-2-acetoxyphenylacetonitrile + NADP+ + H2O enantiopure product formation ?
1.14.13.92 phenylacetone + NADPH + H+ + O2
-
 Thermobifida fusca benzyl acetate + NADP+ + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.13.92 PAMO
-
 Thermobifida fusca

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.13.92 30
-
 assay at Thermobifida fusca

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.13.92 8
-
 assay at Thermobifida fusca

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.13.92 NADPH
-
 Thermobifida fusca