An Efficient Antibody-Catalyzed Aminoacylation Reaction

An antibody generated against a neutral phosphonate diester transition-state analog was found to catalyze the aminoacylation of the 3′-hydroxyl group of thymidine with an alanyl ester. A comparison of the apparent second-order rate constant of the antibody-catalyzed reaction [5.4 × 10$^4$ molar$^{-1...

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Published in:Science (American Association for the Advancement of Science) 1992-04, Vol.256 (5055), p.365-367
Main Authors: Jacobsen, John R., Prudent, James R., Kochersperger, Lynn, Yonkovich, Shirlee, Schultz, Peter G.
Format: Article
Language:English
Subjects:
Acylation
Alanine - metabolism
Alcohols
Amino Acyl-tRNA Synthetases - metabolism
Aminoacyl-tRNA
Antibodies
Antibodies, Monoclonal - metabolism
Biochemistry
Biological and medical sciences
Catalysis
Catalysts
Chlorides
Chromatography, High Pressure Liquid
Enzymes
Esterification
Esters
Fluorescence
Fundamental and applied biological sciences. Psychology
Geometry
Haptens
Haptens - immunology
Hemocyanins - immunology
Kinetics
Mechanisms. Catalysis. Electron transfer. Models
Molecular biophysics
Organic Chemistry
Organophosphonates - immunology
Phosphonic acids
Physical chemistry in biology
Ribonucleic acid
RNA
Serum Albumin, Bovine - immunology
Thymidine - metabolism
Transfer RNA
Viral antibodies
Water
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cited_by cdi_FETCH-LOGICAL-c782t-dfd2e612ff389f4fccf03cf84c856479cfad3d93e0a07d03df627b84b8b6dec63
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container_end_page 367
container_issue 5055
container_start_page 365
container_title Science (American Association for the Advancement of Science)
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creator Jacobsen, John R.
Prudent, James R.
Kochersperger, Lynn
Yonkovich, Shirlee
Schultz, Peter G.
description An antibody generated against a neutral phosphonate diester transition-state analog was found to catalyze the aminoacylation of the 3′-hydroxyl group of thymidine with an alanyl ester. A comparison of the apparent second-order rate constant of the antibody-catalyzed reaction [5.4 × 10$^4$ molar$^{-1}$ minute$^{-1}$ (M$^{-1}$ min$^{-1}$)] with that of the uncatalyzed reaction (2.6 × 10$^{-4}$ M$^{-1}$ min$^{-1}$) revealed this to be a remarkably efficient catalyst. Moreover, although the concentration of water (55 M) greatly exceeds that of the secondary alcohol, the antibody selectively catalyzes acyl transfer to thymidine. The antibody exhibits sequential binding, with Michaelis constants of 770 μM and 260 μM for acyl acceptor and donor, respectively, and a dissociation constant of 240 pM for hapten. This antibody-catalyzed reaction provides increased insight into the requirements for efficient aminoacylation catalysts and may represent a first step toward the generation of "aminoacyl transfer RNA synthetases" with novel specificities.
doi_str_mv 10.1126/science.256.5055.365
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A comparison of the apparent second-order rate constant of the antibody-catalyzed reaction [5.4 × 10$^4$ molar$^{-1}$ minute$^{-1}$ (M$^{-1}$ min$^{-1}$)] with that of the uncatalyzed reaction (2.6 × 10$^{-4}$ M$^{-1}$ min$^{-1}$) revealed this to be a remarkably efficient catalyst. Moreover, although the concentration of water (55 M) greatly exceeds that of the secondary alcohol, the antibody selectively catalyzes acyl transfer to thymidine. The antibody exhibits sequential binding, with Michaelis constants of 770 μM and 260 μM for acyl acceptor and donor, respectively, and a dissociation constant of 240 pM for hapten. 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A comparison of the apparent second-order rate constant of the antibody-catalyzed reaction [5.4 × 10$^4$ molar$^{-1}$ minute$^{-1}$ (M$^{-1}$ min$^{-1}$)] with that of the uncatalyzed reaction (2.6 × 10$^{-4}$ M$^{-1}$ min$^{-1}$) revealed this to be a remarkably efficient catalyst. Moreover, although the concentration of water (55 M) greatly exceeds that of the secondary alcohol, the antibody selectively catalyzes acyl transfer to thymidine. The antibody exhibits sequential binding, with Michaelis constants of 770 μM and 260 μM for acyl acceptor and donor, respectively, and a dissociation constant of 240 pM for hapten. This antibody-catalyzed reaction provides increased insight into the requirements for efficient aminoacylation catalysts and may represent a first step toward the generation of "aminoacyl transfer RNA synthetases" with novel specificities.</abstract><cop>Washington, DC</cop><pub>American Society for the Advancement of Science</pub><pmid>1566082</pmid><doi>10.1126/science.256.5055.365</doi><tpages>3</tpages></addata></record>
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subjects Acylation
Alanine - metabolism
Alcohols
Amino Acyl-tRNA Synthetases - metabolism
Aminoacyl-tRNA
Antibodies
Antibodies, Monoclonal - metabolism
Biochemistry
Biological and medical sciences
Catalysis
Catalysts
Chlorides
Chromatography, High Pressure Liquid
Enzymes
Esterification
Esters
Fluorescence
Fundamental and applied biological sciences. Psychology
Geometry
Haptens
Haptens - immunology
Hemocyanins - immunology
Kinetics
Mechanisms. Catalysis. Electron transfer. Models
Molecular biophysics
Organic Chemistry
Organophosphonates - immunology
Phosphonic acids
Physical chemistry in biology
Ribonucleic acid
RNA
Serum Albumin, Bovine - immunology
Thymidine - metabolism
Transfer RNA
Viral antibodies
Water
title An Efficient Antibody-Catalyzed Aminoacylation Reaction
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