Synthesis of Enantiomerically Pure Ring-Substituted L-Pyridylalanines by Biocatalytic Hydroamination

被引：21

作者：

Ahmed, Syed T. ^{[1
]}

Parmeggiani, Fabio ^{[1
]}

Weise, Nicholas J. ^{[1
]}

Flitsch, Sabine L. ^{[1
]}

Turner, Nicholas J. ^{[1
]}

机构：

[1] Univ Manchester, Manchester Inst Biotechnol, Sch Chem, 131 Princess St, Manchester M1 7DN, Lancs, England

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 21期

基金：

英国生物技术与生命科学研究理事会;

关键词：

PHENYLALANINE AMMONIA-LYASE; AMINO-ACIDS; AZATYROSINE; HYDROGENATION; RESOLUTION; PATHWAY;

D O I：

10.1021/acs.orglett.6b02559

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Current routes to nitrogen-containing heteroarylalanines involve complex multistep synthesis and are often reliant on protection/deprotection steps and wasteful chromatographic purifications. In order to complement existing methodologies, a convenient telescopic strategy was developed for the synthesis of L-pyridylalanine analogues (12 examples) and other L-heteroarylalanines (5 examples) starting from the corresponding aldehydes. A phenylalanine ammonia lyase (PAL) from Anabaena variabilis was used as the biocatalyst to give conversions ranging between 88 and 95%, isolated yields of 32-60%, and perfect enantiopurity (>99% ee) by employing an additional deracemization cascade where necessary.

引用

页码：5468 / 5471

页数：4

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