1.14.13.92: phenylacetone monooxygenase
This is an abbreviated version!
For detailed information about phenylacetone monooxygenase, go to the full flat file.
Word Map on EC 1.14.13.92
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1.14.13.92
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baeyer-villiger
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ketone
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enantioselectivity
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bvmos
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thermobifida
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biocatalytic
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cyclohexanone
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fusca
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synthesis
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sulfoxidations
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biocatalyst
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phosphite
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cyclopentanone
- 1.14.13.92
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baeyer-villiger
- ketone
-
enantioselectivity
-
bvmos
-
thermobifida
-
biocatalytic
- cyclohexanone
- fusca
- synthesis
-
sulfoxidations
-
biocatalyst
- phosphite
- cyclopentanone
Reaction
Synonyms
4-hydroxyacetophenone monooxygenase, Baeyer-Villiger monooxygenase, BVMO, EtaA, HAPMO, M-PAMO, More, PAMO, phenylacetone monooxygenase, Tf PAMO
ECTree
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Reaction
Reaction on EC 1.14.13.92 - phenylacetone monooxygenase
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phenylacetone + NADPH + H+ + O2 = benzyl acetate + NADP+ + H2O
reaction mechanism
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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
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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
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
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phenylacetone + NADPH + H+ + O2 = benzyl acetate + NADP+ + H2O
catalytic mechanism, via C4a-peroxyflavin and Criegee intermediates, of phenylacetone monooxygenases for the native substrate phenylacetone as well as for a linear non-native substrate 2-octanone, using molecular dynamics simulations, quantum mechanics and quantum mechanics/molecular mechanics calculations, and theoretical basis for the preference of the enzyme for the native aromatic substrate over non-native linear substrates, overview
phenylacetone + NADPH + H+ + O2 = benzyl acetate + NADP+ + H2O
the reaction mechanism of BVMO, and particularly PAMO, with native substrate phenylacetone proceeds via the formation of a Criegee intermediate with anionic character, which is subsequently rearranged via the migration of alkyl group to yield the product ester, reaction mechanism, overview. Modeling of the reaction intermediate C4a-peroxyflavin