5.4.3.11: phenylalanine aminomutase (D-beta-phenylalanine forming)
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For detailed information about phenylalanine aminomutase (D-beta-phenylalanine forming), go to the full flat file.
Word Map on EC 5.4.3.11
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5.4.3.11
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pantoea
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synthesis
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agglomerans
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unnatural
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taxus
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stereochemistry
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isomerizes
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isomerization
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drug development
- 5.4.3.11
- pantoea
- synthesis
- agglomerans
-
unnatural
- taxus
-
stereochemistry
-
isomerizes
-
isomerization
- drug development
Reaction
Synonyms
admH, EncP, HitA, methylidene imidazolone-dependent phenylalanine aminomutase, MIO-dependent phenylalanine ammonia lyase, PAM, PaPAM, phenylalanine 2,3-aminomutase, phenylalanine aminomutase, phenylalanine-2,3-aminomutase
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Reaction
Reaction on EC 5.4.3.11 - phenylalanine aminomutase (D-beta-phenylalanine forming)
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L-phenylalanine = D-beta-phenylalanine
reaction mechanism, detailed overview. Proposed elimination mechanisms for the displacement of the NH2-MIO adduct. The final reaction sequence of the MIO-dependent aminomutases involves an alpha,beta-addition reaction, where the NH2-MIO and a proton add across the double bond of the acrylate intermediate. Alternatively, PaPAM can use a stepwise addition sequence where the nucleophile (NH2-MIO) couples to form a 1,4-Michael adduct. This conjugate addition route benefits from an electropositive (delta+) Cbeta by delocalizing the Pi-electrons toward the carboxylate of the substrate
L-phenylalanine = D-beta-phenylalanine
the proposed mechanism of action of PaPAM: starting from either direction with the cooperation of two catalytically essential tyrosine residues (Tyr1 and Tyr2) and the MIO prosthetic group, N-MIO intermediates of alpha- or beta-phenylalanine are formed which interconvert by a alpha - beta migration of the amino group involving a postulated (E)-cinnamate intermediate. PaPAM-catalysed kinetic resolutions starting from racemic alpha-arylalanines or racemic beta-arylalanines result in the opposite enantiomers as products vs. unreacted enantiomers. Mechanism, overview. Formation of significant amounts of (E)-arylacrylates is observed with many substrates indicating substantial lyase-activity of enzyme PaPAM