A stereospecific cyclization catalyzed by an antibody

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

Research output: Contribution to journalArticle

114 Citations (Scopus)

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
DOIs
StatePublished - Jan 1 1987

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Lactones
Cyclization
Catalytic Antibodies
Antibodies
Monoclonal Antibodies
Enzymes

All Science Journal Classification (ASJC) codes

  • General

Cite this

Napper, A. D., Benkovic, S., Tramontano, A., & Lerner, R. A. (1987). A stereospecific cyclization catalyzed by an antibody. Science, 237(4818), 1041-1043. https://doi.org/10.1126/science.3616626
Napper, Andrew D. ; Benkovic, Stephen ; Tramontano, Alfonso ; Lerner, Richard A. / A stereospecific cyclization catalyzed by an antibody. In: Science. 1987 ; Vol. 237, No. 4818. pp. 1041-1043.
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Napper, AD, Benkovic, S, Tramontano, A & Lerner, RA 1987, 'A stereospecific cyclization catalyzed by an antibody', Science, vol. 237, no. 4818, pp. 1041-1043. https://doi.org/10.1126/science.3616626

A stereospecific cyclization catalyzed by an antibody. / Napper, Andrew D.; Benkovic, Stephen; Tramontano, Alfonso; Lerner, Richard A.

In: Science, Vol. 237, No. 4818, 01.01.1987, p. 1041-1043.

Research output: Contribution to journalArticle

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Napper AD, Benkovic S, Tramontano A, Lerner RA. A stereospecific cyclization catalyzed by an antibody. Science. 1987 Jan 1;237(4818):1041-1043. https://doi.org/10.1126/science.3616626