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Science 22 January 1993:
Vol. 259. no. 5094, pp. 490 - 493
DOI: 10.1126/science.8424171
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Articles

Science, Vol 259, Issue 5094, 490-493
Copyright © 1993 by American Association for the Advancement of Science

articles

Antibody catalysis of a disfavored chemical transformation

KD Janda, CG Shevlin, and RA Lerner

Department of Molecular Biology, Scripps Research Institute, La Jolla, CA 92037.

Organic reactions are often limited by stereoelectronic constrains that appear along the reaction coordinate. An antibody has been generated that overcomes these constraints and catalyzes a highly disfavored chemical transformation. The antibody facilitates the difficult 6-endo-tet ring closure of an epoxy-alcohol to form a tetrahydropyran. The catalyzed process is in formal violation of what has become known as Baldwin's rules for ring-closure reactions. In addition to controlling the regiochemistry of the disfavored cyclization reaction, these catalytic antibodies resolve enantiomeric substrates to afford a stereochemically pure product. The principles demonstrated in this study may be applicable to other disfavored chemical processes.


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