Synthesis 2001(6): 0934-0936
DOI: 10.1055/s-2001-13396
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Epoxidation with a Library of Catalytic Antibodies

Yuanwei Chen, Jean-Louis Reymond*
Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, 3012 Bern, Switzerland
Fax: +41(31)6318057; e-Mail: jean-louis.reymond@ioc.unibe.ch;
Further Information

Publication History

Received 1 March 2001
Publication Date:
15 October 2004 (online)

Abstract

Antibody 20B11 raised against a piperidinium hapten 1 catalyzes the epoxidation of unsubstituted olefins such as 2, 3, and 4 by acetonitrile-hydrogen peroxide with partial enantioselectivity. Screening of a library of 46 monoclonal antibodies against a piperidinium hapten 1 for the enantioselective epoxidation of these olefins with the milder oxidation reagent formamide-hydrogen peroxide gave three additional catalytic antibodies, Ab 73B7, Ab 35C12 and Ab77E10, which display complementary enantioselectivities. This work illustrates the diversity of the immune system in providing useful chiral environments for carrying out enantioselective reactions.

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Structural and sequencing studies on this series of antibodies are currently in progress.