2000
DOI: 10.1002/1522-2675(20000906)83:9<2246::aid-hlca2246>3.0.co;2-x
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Mimicking the Reaction of Phenylalanine Ammonia Lyase by a Synthetic Model

Abstract: Dedicated to Professor Albert Eschenmoser on the occasion of his 75th birthday Phenylalanine and histidine ammonia lyases (PAL and HAL) catalyze the reversible conversion of aamino acids to the corresponding acrylic acids by elimination of ammonia. The prosthetic group 3,5-dihydro-5-methylidene-4H-imidazol-4-one (MIO) at the active site of both enzymes supposedly undergoes an electrophilic attack at the aromatic nucleus in the first step of the mechanism of action. Since no chemical analogy existed for such an… Show more

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Cited by 24 publications
(22 citation statements)
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“…Evidence for the active role of the phenyl ring in the process was provided by deactivating the phenyl ring, either by removing the methoxy group or by exchanging it for a nitro group. In these cases no elimination products were detected 62…”
Section: Mechanism Of the Hal And Pal Reactionsmentioning
confidence: 93%
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“…Evidence for the active role of the phenyl ring in the process was provided by deactivating the phenyl ring, either by removing the methoxy group or by exchanging it for a nitro group. In these cases no elimination products were detected 62…”
Section: Mechanism Of the Hal And Pal Reactionsmentioning
confidence: 93%
“…More recently, the chemical feasibility of the electrophile‐assisted elimination of ammonia was demonstrated with a chemical model 62. One portion of the model compound mimicked the essential parts of the substrate (phenylalanine), and another portion mimicked the electrophilic Michael acceptor (MIO) in a sterically appropriate position (Scheme ).…”
Section: Mechanism Of the Hal And Pal Reactionsmentioning
confidence: 99%
See 1 more Smart Citation
“…Die chemische Plausibilität der elektrophil unterstützten Eliminierung von Ammoniak wurde anhand eines chemischen Modells untermauert 62. Einige Teile der Modellverbindung imitierten den wesentlichen Teil des Substrates, andere den elektrophilen Michael‐Acceptor (MIO) in einer sterisch günstigen Stellung (Schema ).…”
Section: Zum Mechanismus Der Hal‐ Und Pal‐reaktionunclassified
“…Although some of the results support such a mechanism, chemical analogies with the Friedel–Crafts‐like intermediate are also possible;6 kinetic data of the interaction of various heteroaryl alanines with PAL from parsley,7 and more recent works, especially X‐ray structures of ammonia lyases with bonded substrates and inhibitors, seem to favor a mechanism in which the α‐amino group of the substrate is bound to MIO 8. However, it is known that the enzymes may not crystallize in their active conformation.…”
Section: Introductionmentioning
confidence: 99%