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Literature summary extracted from

  • Zambianchi, F.; Fraaije, M.W.; Carrea, G.; de Gonzalo, G.; Rodriguez, C.; Gotor, V.; Ottolina, G.
    Titration and assignment of residues that regulate the enantioselectivity of phenylacetone monooxygenase (2007), Adv. Synth. Catal., 349, 1327-1331.
No PubMed abstract available

Application

EC Number Application Comment Organism
1.14.13.92 synthesis usage of the enzyme for asymmetric sulfooxidation of thioanisole and of racemic 2-phenylpropionaldehyde in a Baeyer-Villiger oxidation reaction 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 Q47PU3
-
-

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 2-phenylpropionaldehyde + NADPH + H+ + O2
-
 Thermobifida fusca ?
-
 ?
1.14.13.92 additional information PAMO is an FAD-containing Baeyer-Villiger monooxygenase, two different residues are responsible for the pH effects on PAMO enantioselectivity, protonation of Arg337 and the FAD:C4a-hydroperoxide/FAD:C4a-peroxide equilibrium are the major factors responsible for the fine-tuning of PAMO enantioselectivity in Baeyer-Villiger oxidation and sulfooxidation, respectively Thermobifida fusca ?
-
 ?
1.14.13.92 phenylacetone + NADPH + H+ + O2
-
 Thermobifida fusca benzyl acetate + NADP+ + H2O
-
 ?
1.14.13.92 phenylacetone + NADPH + H+ + O2 enantioselective reaction, regulation mechanism, overview Thermobifida fusca benzyl acetate + NADP+ + H2O
-
 ?
1.14.13.92 thioanisole + NADPH + H+ + O2 the asymmetric oxidation of thioanisole to sulfoxide is accompanied by the overoxidation to achiral sulfone Thermobifida fusca ?
-
 ?

Subunits

EC Number Subunits Comment Organism
1.14.13.92 More model of the three-dimensional structure of PAMO, overview Thermobifida fusca

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 27
-
 assay at Thermobifida fusca

pH Range

EC Number pH Minimum pH Maximum Comment Organism
1.14.13.92 7 10 pH profile, and dependence of the enantioselectivity of the reaction, overview Thermobifida fusca

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.13.92 NADPH
-
 Thermobifida fusca