Remarkably efficient hydrolysis of a 4-nitrophenyl ester by a catalytic antibody raised to an ammonium hapten

Abedawn I. Khalaf, George R. Proctor, Colin J. Suckling, Laura H. Bence, June I. Irvine, William H. Stimson

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Antibodies were raised to a 1-benzazepine hapten (I) and the properties of 2 of the strongly binding clones, designated C3 and C5, as catalysts examd. Neither antibody catalyzed the reaction for which they were first generated, electrophilic substitution in the benzene ring, but C3 catalyzed the hydrolysis of an aralkyl 4-nitrophenyl ester with a rate enhancement of >106 compared with the background solvolysis rate. The mechanism of the hydrolysis reaction seems to involve general base catalysis on the basis of chem. modification expts. and isotope effects on the reaction rate in D2O. The possibility that C3 might catalyze other reactions (elimination, deuterium exchange, and epoxide opening) was investigated but no other reactions were obsd. In contrast, C5 catalyzed none of the reactions investigated. The properties of the 2 antibodies are discussed with respect to their ability to bind compds. structurally related to the hapten.
Original languageEnglish
Pages (from-to)1475-1481
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number12
DOIs
Publication statusPublished - 1992

Fingerprint

Catalytic Antibodies
Haptens
Ammonium Compounds
Hydrolysis
Esters
Antibodies
Benzazepines
Deuterium
Epoxy Compounds
Benzene
Isotopes
Catalysis
Reaction rates
Substitution reactions
Catalysts
4-nitrophenyl

Keywords

  • 4-nitrophenyl ester
  • catalytic antibody
  • ammonium hapten

Cite this

@article{aa9ee6ea2ccf417e9c1dad45b86de719,
title = "Remarkably efficient hydrolysis of a 4-nitrophenyl ester by a catalytic antibody raised to an ammonium hapten",
abstract = "Antibodies were raised to a 1-benzazepine hapten (I) and the properties of 2 of the strongly binding clones, designated C3 and C5, as catalysts examd. Neither antibody catalyzed the reaction for which they were first generated, electrophilic substitution in the benzene ring, but C3 catalyzed the hydrolysis of an aralkyl 4-nitrophenyl ester with a rate enhancement of >106 compared with the background solvolysis rate. The mechanism of the hydrolysis reaction seems to involve general base catalysis on the basis of chem. modification expts. and isotope effects on the reaction rate in D2O. The possibility that C3 might catalyze other reactions (elimination, deuterium exchange, and epoxide opening) was investigated but no other reactions were obsd. In contrast, C5 catalyzed none of the reactions investigated. The properties of the 2 antibodies are discussed with respect to their ability to bind compds. structurally related to the hapten.",
keywords = "4-nitrophenyl ester , catalytic antibody , ammonium hapten",
author = "Khalaf, {Abedawn I.} and Proctor, {George R.} and Suckling, {Colin J.} and Bence, {Laura H.} and Irvine, {June I.} and Stimson, {William H.}",
year = "1992",
doi = "10.1039/P19920001475",
language = "English",
pages = "1475--1481",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
number = "12",

}

Remarkably efficient hydrolysis of a 4-nitrophenyl ester by a catalytic antibody raised to an ammonium hapten. / Khalaf, Abedawn I.; Proctor, George R.; Suckling, Colin J.; Bence, Laura H.; Irvine, June I.; Stimson, William H.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 12, 1992, p. 1475-1481.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Remarkably efficient hydrolysis of a 4-nitrophenyl ester by a catalytic antibody raised to an ammonium hapten

AU - Khalaf, Abedawn I.

AU - Proctor, George R.

AU - Suckling, Colin J.

AU - Bence, Laura H.

AU - Irvine, June I.

AU - Stimson, William H.

PY - 1992

Y1 - 1992

N2 - Antibodies were raised to a 1-benzazepine hapten (I) and the properties of 2 of the strongly binding clones, designated C3 and C5, as catalysts examd. Neither antibody catalyzed the reaction for which they were first generated, electrophilic substitution in the benzene ring, but C3 catalyzed the hydrolysis of an aralkyl 4-nitrophenyl ester with a rate enhancement of >106 compared with the background solvolysis rate. The mechanism of the hydrolysis reaction seems to involve general base catalysis on the basis of chem. modification expts. and isotope effects on the reaction rate in D2O. The possibility that C3 might catalyze other reactions (elimination, deuterium exchange, and epoxide opening) was investigated but no other reactions were obsd. In contrast, C5 catalyzed none of the reactions investigated. The properties of the 2 antibodies are discussed with respect to their ability to bind compds. structurally related to the hapten.

AB - Antibodies were raised to a 1-benzazepine hapten (I) and the properties of 2 of the strongly binding clones, designated C3 and C5, as catalysts examd. Neither antibody catalyzed the reaction for which they were first generated, electrophilic substitution in the benzene ring, but C3 catalyzed the hydrolysis of an aralkyl 4-nitrophenyl ester with a rate enhancement of >106 compared with the background solvolysis rate. The mechanism of the hydrolysis reaction seems to involve general base catalysis on the basis of chem. modification expts. and isotope effects on the reaction rate in D2O. The possibility that C3 might catalyze other reactions (elimination, deuterium exchange, and epoxide opening) was investigated but no other reactions were obsd. In contrast, C5 catalyzed none of the reactions investigated. The properties of the 2 antibodies are discussed with respect to their ability to bind compds. structurally related to the hapten.

KW - 4-nitrophenyl ester

KW - catalytic antibody

KW - ammonium hapten

U2 - 10.1039/P19920001475

DO - 10.1039/P19920001475

M3 - Article

SP - 1475

EP - 1481

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

SN - 1472-7781

IS - 12

ER -