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Chemistry. 2002 Dec 2;8(23):5288-95.

Thiamin-diphosphate-dependent enzymes: new aspects of asymmetric C-C bond formation.

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  • 1Institut für Enzymtechnologie Heinrich-Heine-Universität Düsseldorf 52426 Düsseldorf, Germany.

Abstract

Starting from a thorough investigation of mechanistic aspects of ThDP-dependent (ThDP = thiamin diphosphate) enzymes in combination with mutagenesis studies and a detailed substrate screening, new general synthetic methods have been developed based on Umpolung reactions by thiamin catalysis. A selective donor-acceptor concept was established leading to the first asymmetric cross-benzoin condensation, and a kinetic racemic resolution through C-C bond cleavage was developed. With these tools and in combination with protein engineering, we approached the synthesis of new chiral building blocks on a preparative scale. An outlook is given with respect to the potential of other ThDP-dependent enzymes as catalysts in asymmetric synthesis.

PMID:
12432496
[PubMed - indexed for MEDLINE]
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