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Science 28 August 1987:
Vol. 237. no. 4818, pp. 1041 - 1043
DOI: 10.1126/science.3616626
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Articles

Science, Vol 237, Issue 4818, 1041-1043
Copyright © 1987 by American Association for the Advancement of Science

articles

A stereospecific cyclization catalyzed by an antibody

AD Napper, SJ Benkovic, A Tramontano, and RA Lerner

A monoclonal antibody elicited by a transition-state analog that is representative of an intramolecular six-membered ring cyclization reaction acted as a stereospecific, enzyme-like catalyst for the appropriate substrate. Formation of a single enantiomer of a delta-lactone from the corresponding racemic delta-hydroxyester was accelerated by the antibody by about a factor of 170, which permitted isolation of the lactone in an enantiomeric excess of about 94 percent. This finding demonstrates the feasibility of catalytic-antibody generation for chemical transformations that require stereochemical control.




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Science. ISSN 0036-8075 (print), 1095-9203 (online)