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The Interaction of Heteroaryl‐Acrylates and Alanines with Phenylalanine Ammonia‐Lyase from Parsley
Author(s) -
Paizs Csaba,
Katona Adrian,
Rétey János
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501034
Subject(s) - chemistry , enantiomer , electrophile , phenylalanine , ammonia , alanine , furan , phenylalanine ammonia lyase , substrate (aquarium) , stereochemistry , enantiomeric excess , friedel–crafts reaction , organic chemistry , medicinal chemistry , amino acid , enantioselective synthesis , catalysis , biochemistry , oceanography , geology
Acrylic acids and alanines substituted with heteroaryl groups at the β‐position were synthesized and spectroscopically characterized (UV, HRMS, 1 H NMR, and 13 C NMR spectroscopy). The heteroaryl groups were furanyl, thiophenyl, benzofuranyl, and benzothiophenyl and contained the alanyl side chains either at the 2‐ or 3‐positions. While the former are good substrates for phenylalanine ammonia‐lyase (PAL), the latter compounds are inhibitors. Exceptions are thiophen‐3‐yl‐alanine, a moderate substrate and furan‐3‐yl‐alanine, which is inert. Possible reasons for these exceptions are discussed. Starting from racemic heteroaryl‐2‐alanines their D ‐enantiomers were prepared by using a stereodestructive procedure. From the heteroaryl‐2‐acrylates, the L ‐enantiomers of the heteroaryl‐2‐alanines were prepared at high ammonia concentration. These results can be best explained by a Friedel–Crafts‐type electrophilic attack at the aromatic part of the substrates as the initial step of the PAL reaction.