A stereospecific cyclization catalyzed by an antibody

Andrew D. Napper, Stephen J. Benkovic, Alfonso Tramontano, Richard A. Lerner

Research output: Contribution to journalArticle

114 Scopus citations

Abstract

A monoclonal antibody elicited by a transition-state analog that is representative of an intramolecular six-membercd ring cyclization reaction acted as a stercospecific, enzyme-like catalyst for the appropriate substrate. Formation of a single enantiomer of a 5-lactone from the corresponding racemic 8-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.

Original languageEnglish (US)
Pages (from-to)1041-1043
Number of pages3
JournalScience
Volume237
Issue number4818
StatePublished - 1987
Externally publishedYes

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    Napper, A. D., Benkovic, S. J., Tramontano, A., & Lerner, R. A. (1987). A stereospecific cyclization catalyzed by an antibody. Science, 237(4818), 1041-1043.