5.4.3.10: phenylalanine aminomutase (L-beta-phenylalanine forming)
This is an abbreviated version!
For detailed information about phenylalanine aminomutase (L-beta-phenylalanine forming), go to the full flat file.
Word Map on EC 5.4.3.10
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5.4.3.10
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taxus
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ammonia
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enantioselectivity
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stereochemistry
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regioselectivity
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enantiopure
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pantoea
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chinensis
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biocatalytic
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isomerizes
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agglomerans
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isomerization
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prosthesis
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trans-cinnamic
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e-cinnamate
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enantiomeric
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biocatalyst
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unnatural
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acrylate
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canadensis
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rebind
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pro-3s
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beta-amino
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lyases
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non-natural
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lyase-like
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n-benzoyl
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intramolecularly
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beta-isomer
- 5.4.3.10
- taxus
- ammonia
-
enantioselectivity
-
stereochemistry
-
regioselectivity
-
enantiopure
- pantoea
- chinensis
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biocatalytic
-
isomerizes
- agglomerans
-
isomerization
-
prosthesis
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trans-cinnamic
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e-cinnamate
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enantiomeric
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biocatalyst
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unnatural
- acrylate
- canadensis
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rebind
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pro-3s
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beta-amino
- lyases
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non-natural
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lyase-like
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n-benzoyl
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intramolecularly
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beta-isomer
Reaction
Synonyms
(R)-PAM, (R)-selective PAM, admH, CctP, More, PAM, phenylalanine AM, phenylalanine aminomutase, phenylalanine-2,3-aminomutase, TcPAM
ECTree
5.4.3.10 phenylalanine aminomutase (L-beta-phenylalanine forming)Advanced search results
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results (Substrates Products
Substrates Products on EC 5.4.3.10 - phenylalanine aminomutase (L-beta-phenylalanine forming)
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3'-methyl-alpha-phenylalanine
3'-methyl-beta-phenylalanine
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plus 3'-methylcinnamate, product of ammonia lyase reaction. Distribution of 3'-methyl-beta-phenylalanine and 3'-methylcinnamate is at about 1:1
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?
4'-methyl-alpha-phenylalanine
4'-methyl-beta-phenylalanine
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plus 4'-methylcinnamate, product of ammonia lyase reaction
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?
D-alpha-phenylalanine
L-beta-phenylalanine
(S)-alpha-phenylalanine, reaction mechanism
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r
L-phenylalanine
L-beta-phenylalanine
L-alpha-phenylalanine
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r
additional information
?
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(E)-cinnamate is both a substrate and an intermediate of the reaction. To account for the distinct (3alpha)-beta-amino acid stereochemistry catalyzed by the enzyme, the cinnamate skeleton must rotate the C1-Calpha and Cipso-Cbeta bonds 180° in the active site prior to exchange and rebinding of theNH2/H pair to the cinnamate
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-
?
additional information
?
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-
(E)-cinnamate is both a substrate and an intermediate of the reaction. To account for the distinct (3alpha)-beta-amino acid stereochemistry catalyzed by the enzyme, the cinnamate skeleton must rotate the C1-Calpha and Cipso-Cbeta bonds 180° in the active site prior to exchange and rebinding of theNH2/H pair to the cinnamate
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-
?
additional information
?
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the enzyme catalyzes a 2,3-amine shift that reversibly interconverts alpha-Phe to beta-Phe
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-
?
additional information
?
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phenylalanine-2,3-aminomutase (PAM) from Taxus chinensis, a 4-methylidene-imidazole-5-one (MIO)-dependent enzyme, catalyzes the reversible conversion of (S)-alpha-phenylalanine into (R)-beta-phenylalanine via trans-cinnamic acid. The enzyme also catalyzes the direct addition of ammonia to trans-cinnamic acid, a reaction that can be used for the preparation of beta-amino acids, cf. EC 4.3.1.24, phenylalanine ammonia-lyase
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-
?
additional information
?
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phenylalanine-2,3-aminomutase (PAM) from Taxus chinensis, a 4-methylidene-imidazole-5-one (MIO)-dependent enzyme, catalyzes the reversible conversion of (S)-alpha-phenylalanine into (R)-beta-phenylalanine via trans-cinnamic acid. The enzyme also catalyzes the direct addition of ammonia to trans-cinnamic acid, a reaction that can be used for the preparation of beta-amino acids, cf. EC 4.3.1.24, phenylalanine ammonia-lyase
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-
?
additional information
?
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TcPAM catalyzes the isomerization of alpha-phenylalanine to beta-phenylalanine through exchanging the position of the amine group (Calpha -> Cbeta) and pro-3S hydrogen proton (Cbeta -> Calpha) with retention of the configuration at the reaction termini, which requires reorientation after deamination of beta-phenylalanine to trans-cinnamic acid in which the reface of the Cbeta and the si-face of the Cbeta carton atoms are positioned for amine readdition and reprotonation. The enzyme TcPAM also catalyzes the regioselective hydroamination of trans-cinnamic acid (t-CA) to yield L-beta-Phe, TcPAL, EC 4.3.1.24. The final product mixture consists of both alpha- and beta-Phe owing to low regioselectivity of the enzyme
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-
?
additional information
?
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TcPAM catalyzes the isomerization of alpha-phenylalanine to beta-phenylalanine through exchanging the position of the amine group (Calpha -> Cbeta) and pro-3S hydrogen proton (Cbeta -> Calpha) with retention of the configuration at the reaction termini, which requires reorientation after deamination of beta-phenylalanine to trans-cinnamic acid in which the reface of the Cbeta and the si-face of the Cbeta carton atoms are positioned for amine readdition and reprotonation. The enzyme TcPAM also catalyzes the regioselective hydroamination of trans-cinnamic acid (t-CA) to yield L-beta-Phe, TcPAL, EC 4.3.1.24. The final product mixture consists of both alpha- and beta-Phe owing to low regioselectivity of the enzyme
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-
?
additional information
?
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the enzyme catalyzes a 2,3-amine shift that reversibly interconverts alpha-Phe to beta-Phe
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-
?
