On the specificity of reactions catalysed by the antibody H11

Abedawn I. Khalaf; Sabin Linaza; Andrew R. Pitt; William H. Stimson; Colin J. Suckling

doi:10.1016/S0040-4020(99)01037-6

On the specificity of reactions catalysed by the antibody H11

Abedawn I. Khalaf, Sabin Linaza, Andrew R. Pitt, William H. Stimson, Colin J. Suckling^*

^*Corresponding author for this work

Analytical, Measurements and Physical Chemistry

University of Strathclyde

Research output: Contribution to journal › Article › peer-review

Abstract

The substrate specificity and the stereochemical course of the reactions catalysed by the antibody H11 (which was raised to a protein conjugated derivative of the adduct of 1-acetoxy-buta-1,3-diene 1) have been investigated. The antibody shows high selectivity for acetoxybutadiene which it hydrolyses to the corresponding dienol, the major diene component of the cycloaddition reactions observed. However, it tolerates a range of N- alkylmaleimides. The stereochemical course of cycloaddition is shown to produce a significant enantiomeric excess of the 3aR, 4S, 7aR-endo- diastereoisomer by analysis with Mosher's ester derivatives. This study also revealed that H11 is capable of slowly catalysing the hydrolysis of N- alkylmaleimide substrates. The implications for the mechanism of action of H11 are discussed.

Original language	English
Pages (from-to)	489-495
Number of pages	7
Journal	Tetrahedron
Volume	56
Issue number	3
DOIs	https://doi.org/10.1016/S0040-4020(99)01037-6
Publication status	Published - 14 Jan 2000

Keywords

Acetoxybutadiene
Antibody H11
Mosher's ester

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10.1016/S0040-4020(99)01037-6

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title = "On the specificity of reactions catalysed by the antibody H11",

abstract = "The substrate specificity and the stereochemical course of the reactions catalysed by the antibody H11 (which was raised to a protein conjugated derivative of the adduct of 1-acetoxy-buta-1,3-diene 1) have been investigated. The antibody shows high selectivity for acetoxybutadiene which it hydrolyses to the corresponding dienol, the major diene component of the cycloaddition reactions observed. However, it tolerates a range of N- alkylmaleimides. The stereochemical course of cycloaddition is shown to produce a significant enantiomeric excess of the 3aR, 4S, 7aR-endo- diastereoisomer by analysis with Mosher's ester derivatives. This study also revealed that H11 is capable of slowly catalysing the hydrolysis of N- alkylmaleimide substrates. The implications for the mechanism of action of H11 are discussed. ",

keywords = "Acetoxybutadiene, Antibody H11, Mosher's ester",

author = "Khalaf, {Abedawn I.} and Sabin Linaza and Pitt, {Andrew R.} and Stimson, {William H.} and Suckling, {Colin J.}",

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T1 - On the specificity of reactions catalysed by the antibody H11

AU - Khalaf, Abedawn I.

AU - Linaza, Sabin

AU - Pitt, Andrew R.

AU - Stimson, William H.

AU - Suckling, Colin J.

PY - 2000/1/14

Y1 - 2000/1/14

N2 - The substrate specificity and the stereochemical course of the reactions catalysed by the antibody H11 (which was raised to a protein conjugated derivative of the adduct of 1-acetoxy-buta-1,3-diene 1) have been investigated. The antibody shows high selectivity for acetoxybutadiene which it hydrolyses to the corresponding dienol, the major diene component of the cycloaddition reactions observed. However, it tolerates a range of N- alkylmaleimides. The stereochemical course of cycloaddition is shown to produce a significant enantiomeric excess of the 3aR, 4S, 7aR-endo- diastereoisomer by analysis with Mosher's ester derivatives. This study also revealed that H11 is capable of slowly catalysing the hydrolysis of N- alkylmaleimide substrates. The implications for the mechanism of action of H11 are discussed.

AB - The substrate specificity and the stereochemical course of the reactions catalysed by the antibody H11 (which was raised to a protein conjugated derivative of the adduct of 1-acetoxy-buta-1,3-diene 1) have been investigated. The antibody shows high selectivity for acetoxybutadiene which it hydrolyses to the corresponding dienol, the major diene component of the cycloaddition reactions observed. However, it tolerates a range of N- alkylmaleimides. The stereochemical course of cycloaddition is shown to produce a significant enantiomeric excess of the 3aR, 4S, 7aR-endo- diastereoisomer by analysis with Mosher's ester derivatives. This study also revealed that H11 is capable of slowly catalysing the hydrolysis of N- alkylmaleimide substrates. The implications for the mechanism of action of H11 are discussed.

KW - Acetoxybutadiene

KW - Antibody H11

KW - Mosher's ester

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U2 - 10.1016/S0040-4020(99)01037-6

DO - 10.1016/S0040-4020(99)01037-6

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SN - 0040-4020

VL - 56

SP - 489

EP - 495

JO - Tetrahedron

JF - Tetrahedron

IS - 3

ER -

On the specificity of reactions catalysed by the antibody H11

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