Synfacts 2007(2): 0208-0208  
DOI: 10.1055/s-2006-955791
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Stereochemically Complementary Biocatalysts Created by Directed Evolution

Contributor(s): Benjamin List, Daniela Kampen
G. J. Williams, T. Woodhall, L. M. Farnsworth, A. Nelson*, A. Berry
University of Leeds, UK
Further Information

Publication History

Publication Date:
23 January 2007 (online)

Significance

A pair of stereochemically complementary biocatalysts for the synthesis of sialic acid mimetics has been created. Directed evolution using both error-prone PCR as well as saturation mutagenesis starting from the E192N variant of wild-type enzyme N-acetylneuramic acid lyase (NAL) has provided S-selective E192N/T167G and R-selective E192N/T167V/S208V, respectively. These mutants mediate the aldol reaction of aldehyde 1 and pyruvate 2 to give 4S- and 4R-configured dipropylamides 3 and 4 in moderate yields and high diastereoselectivities.