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Literature summary for 1.14.13.92 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

Application Comment Organism
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)

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

Organism

Organism UniProt Comment Textmining
Thermobifida fusca Q47PU3
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-

Reaction

Reaction Comment Organism Reaction ID
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

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-phenylpropionaldehyde + NADPH + H+ + O2
-
Thermobifida fusca ?
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?
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 ?
-
?
phenylacetone + NADPH + H+ + O2
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Thermobifida fusca benzyl acetate + NADP+ + H2O
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?
phenylacetone + NADPH + H+ + O2 enantioselective reaction, regulation mechanism, overview Thermobifida fusca benzyl acetate + NADP+ + H2O
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?
thioanisole + NADPH + H+ + O2 the asymmetric oxidation of thioanisole to sulfoxide is accompanied by the overoxidation to achiral sulfone Thermobifida fusca ?
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?

Subunits

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

Synonyms

Synonyms Comment Organism
PAMO
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Thermobifida fusca

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
27
-
assay at Thermobifida fusca

pH Range

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

Cofactor

Cofactor Comment Organism Structure
NADPH
-
Thermobifida fusca