Asymmetric synthesis of l-thienylalanines

l-Thienylalanines were prepared via the hydantoin and azlactone routes with the key step consisting of the microbial transamination of 2-hydroxy-3-thienylacrylic with l-aspartic acid as amino donor. The transamination reaction was performed by a genetically engineered E. coli strain on scales up to...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1997-02, Vol.8 (4), p.527-536
Main Authors: Meiwes, Johannes, Schudok, Manfred, Kretzschmar, Gerhard
Format: Article
Language:English
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Summary:l-Thienylalanines were prepared via the hydantoin and azlactone routes with the key step consisting of the microbial transamination of 2-hydroxy-3-thienylacrylic with l-aspartic acid as amino donor. The transamination reaction was performed by a genetically engineered E. coli strain on scales up to 100 g of l-3-(2-thienyl)alanine 1a and is also applicable to the preparation of the isomeric amino acid 1b and some ring-substituted derivatives. Efficient 3-step synthesis of non-proteinogenic, enantiomerically pure L-thienylalanines. The transamination of 2-hydroxy-3-thienyl-acrylic acids involves whole cells of a genetically engineered bacterial strain.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(97)00016-5