Volume 22, Issue 15
Preparative Organic Chemistry
Full Access

ChemInform Abstract: Catalytic Antibodies with Acyl-Transfer Capabilities: Mechanistic and Kinetic Investigations.

K. D. JANDA

K. D. JANDA

Dep. Mol. Biol., Scripps Clin. Res. Found., La Jolla, CA 92037, USA

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J. A. ASHLEY

J. A. ASHLEY

Dep. Mol. Biol., Scripps Clin. Res. Found., La Jolla, CA 92037, USA

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T. M. JONES

T. M. JONES

Dep. Mol. Biol., Scripps Clin. Res. Found., La Jolla, CA 92037, USA

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D. A. MCLEOD

D. A. MCLEOD

Dep. Mol. Biol., Scripps Clin. Res. Found., La Jolla, CA 92037, USA

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D. M. SCHLOEDER

D. M. SCHLOEDER

Dep. Mol. Biol., Scripps Clin. Res. Found., La Jolla, CA 92037, USA

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M. I. WEINHOUSE

M. I. WEINHOUSE

Dep. Mol. Biol., Scripps Clin. Res. Found., La Jolla, CA 92037, USA

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R. A. LERNER

R. A. LERNER

Dep. Mol. Biol., Scripps Clin. Res. Found., La Jolla, CA 92037, USA

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R. A. GIBBS

R. A. GIBBS

Dep. Mol. Biol., Scripps Clin. Res. Found., La Jolla, CA 92037, USA

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P. A. BENKOVIC

P. A. BENKOVIC

Dep. Mol. Biol., Scripps Clin. Res. Found., La Jolla, CA 92037, USA

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R. HILHORST

R. HILHORST

Dep. Mol. Biol., Scripps Clin. Res. Found., La Jolla, CA 92037, USA

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S. J. BENKOVIC

S. J. BENKOVIC

Dep. Mol. Biol., Scripps Clin. Res. Found., La Jolla, CA 92037, USA

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First published: April 16, 1991

Abstract

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ChemInform Abstract

An extended study is presented on three different monoclonal antibodies (2H6, 21H3 and 43C9) that catalyze the hydrolysis of an alkyl ester and an aryl amide bond. New substrates (I) and (II) are synthesized and buffer-assisted reactions are employed to determine antibody-substrate fidelity. The catalytic antibodies are shown to be extremely specific with respect to both substrate and nucleophile and will permit only little latitude in choice of potential substrates. 18O-incorporation experiments are performed providing evidence that these antibody-mediated reactions proceed through attack at the acyl carbonyl.

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