2013
DOI: 10.1002/cctc.201200536
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The Interaction of Nitrophenylalanines with Wild Type and Mutant 4‐Methylideneimidazole‐5‐one‐less Phenylalanine Ammonia Lyase

Abstract: Racemic nitrophenylalanines and (E)‐nitrophenylacrylates are synthesized from the corresponding aldehydes. Both products are important for the examination of the mechanism of action of phenylalanine ammonia lyase (PAL). For the reaction of the rac‐nitrophenylalanines with both wild type (wt) PAL and an 4‐methylideneimidazole‐5‐one (MIO)‐less mutant, the kinetic constants Km and Vmax are determined and compared with those of the natural substrate L‐phenylalanine: the Km values for the racemic nitrophenylalanine… Show more

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Cited by 2 publications
(5 citation statements)
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“…More recently, Retey and coworkers demonstrated the conversion of nitrophenylalanine with PcPAL, in both the deamination and the amination directions, showing also that the MIO-less mutant PcPAL-Ser202Ala is active on such substrates, even with considerably higher specific activities than the natural substrates. 153 This was thought to be further evidence of a Friedel−Crafts-like mechanism, since the strong electron-withdrawing effect of the nitro group provides the same activation as that provided by the MIO moiety after the Friedel−Crafts-type attack. Very recently, however, we showed evidence of a MIO-independent competing reaction pathway with highly activated substrates (i.e., those carrying strong EWGs) that proceeds nonstereoselectively and more slowly.…”
Section: Structure and Mechanism Of Aromatic Amino Acid Ammonia-lyase...mentioning
confidence: 99%
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“…More recently, Retey and coworkers demonstrated the conversion of nitrophenylalanine with PcPAL, in both the deamination and the amination directions, showing also that the MIO-less mutant PcPAL-Ser202Ala is active on such substrates, even with considerably higher specific activities than the natural substrates. 153 This was thought to be further evidence of a Friedel−Crafts-like mechanism, since the strong electron-withdrawing effect of the nitro group provides the same activation as that provided by the MIO moiety after the Friedel−Crafts-type attack. Very recently, however, we showed evidence of a MIO-independent competing reaction pathway with highly activated substrates (i.e., those carrying strong EWGs) that proceeds nonstereoselectively and more slowly.…”
Section: Structure and Mechanism Of Aromatic Amino Acid Ammonia-lyase...mentioning
confidence: 99%
“…237 Nitro-substituted phenylalanines were also obtained in very good yields. 139,153 Access to such a broad variety of compounds through one simple biocatalytic method (with excellent enantiomeric purity in all cases) opened up potential sustainable routes to the manufacture of countless non-natural amino acid derivatives for the pharmaceutical and agrochemical industry. PcPAL showed remarkable thermal stability compared to the free enzyme: no significant loss of activity at 70°C for 38 h, with an optimum temperature found to be around 60°C (1.5-fold increase in temperature tolerance compared to the free enzyme).…”
Section: Synthesis Of L-arylalaninesmentioning
confidence: 99%
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