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首页> 外文期刊>Chemistry: A European journal >The Interaction of Heteroaryl-Acrylates and Alanines with Phenylalanine Ammonia-Lyase from Parsley
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The Interaction of Heteroaryl-Acrylates and Alanines with Phenylalanine Ammonia-Lyase from Parsley

机译：杂芳基丙烯酸酯和丙氨酸与欧芹苯丙氨酸氨解酶的相互作用

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摘要

Acrylic acids and alanines substituted with heteroaryl groups at the beta-position were synthesized and spectroscopically characterized(UV,HRMS,~1HNMR,and ~(13)CNMR spec-troscopy).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 ammonialyase(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 stereode-structive procedure.From the heteroar-yl-2-acrylates,the L-enantiomers of the heteroaryl-2-alanines were prepared at high ammonia concentration.These results can be best explained by a Frie-del-Crafts-type electrophilic attack at the aromatic part of the substrates as the initial step of the PAL reaction.
机译：合成了在β位置被杂芳基取代的丙烯酸和丙氨酸，并进行了光谱表征（UV，HRMS，〜1HNMR和〜（13）CNMR光谱）。杂芳基为呋喃基，噻吩基，苯并呋喃基和苯并噻吩基在2或3位上都含有丙氨酸侧链。前者是苯丙氨酸解氨酶（PAL）的良好底物，后一种化合物是抑制剂。噻吩-3-基-丙氨酸是中等底物和呋喃- 3-基丙氨酸是惰性的。讨论了这些例外的可能原因。从外消旋杂芳基-2-丙氨酸开始，它们的D-对映体是通过立体构筑方法制备的。杂芳基-2-丙氨酸的L对映异构体是在高氨浓度下制备的，这些结果可以用Frie-del-Crafts型亲电性攻击底物的芳族部分作为PAL反应的初始步骤来最好地解释。 。

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