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

Pure And Applied Chemistry

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

7 Citations (Scopus)

Abstract

The substrate specificity and the stereochem. course of the reactions catalyzed by the antibody H11 (which was raised to a protein conjugated deriv. of the adduct of 1-acetoxy-buta-1,3-diene 1) have been investigated. The antibody shows high selectivity for acetoxybutadiene which it hydrolyzes to the corresponding dienol, the major diene component of the cycloaddn. reactions obsd. However, it tolerates a range of N-alkylmaleimides. The stereochem. course of cycloaddn. is shown to produce a significant enantiomeric excess of the 3aR,4S,7aR-endo-diastereoisomer by anal. with Mosher's ester derivs. This study also revealed that H11 is capable of slowly catalyzing the hydrolysis of N-alkylmaleimide substrates. The implications for the mechanism of action of H11 are discussed. [on SciFinder(R)]

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

antibody H11
acetoxybutadiene
Mosher's ester
pure and applied chemistry

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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 stereochem. course of the reactions catalyzed by the antibody H11 (which was raised to a protein conjugated deriv. of the adduct of 1-acetoxy-buta-1,3-diene 1) have been investigated. The antibody shows high selectivity for acetoxybutadiene which it hydrolyzes to the corresponding dienol, the major diene component of the cycloaddn. reactions obsd. However, it tolerates a range of N-alkylmaleimides. The stereochem. course of cycloaddn. is shown to produce a significant enantiomeric excess of the 3aR,4S,7aR-endo-diastereoisomer by anal. with Mosher's ester derivs. This study also revealed that H11 is capable of slowly catalyzing the hydrolysis of N-alkylmaleimide substrates. The implications for the mechanism of action of H11 are discussed. [on SciFinder(R)]",

keywords = "antibody H11, acetoxybutadiene, Mosher's ester, pure and applied chemistry",

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

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doi = "10.1016/S0040-4020(99)01037-6",

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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 stereochem. course of the reactions catalyzed by the antibody H11 (which was raised to a protein conjugated deriv. of the adduct of 1-acetoxy-buta-1,3-diene 1) have been investigated. The antibody shows high selectivity for acetoxybutadiene which it hydrolyzes to the corresponding dienol, the major diene component of the cycloaddn. reactions obsd. However, it tolerates a range of N-alkylmaleimides. The stereochem. course of cycloaddn. is shown to produce a significant enantiomeric excess of the 3aR,4S,7aR-endo-diastereoisomer by anal. with Mosher's ester derivs. This study also revealed that H11 is capable of slowly catalyzing the hydrolysis of N-alkylmaleimide substrates. The implications for the mechanism of action of H11 are discussed. [on SciFinder(R)]

AB - The substrate specificity and the stereochem. course of the reactions catalyzed by the antibody H11 (which was raised to a protein conjugated deriv. of the adduct of 1-acetoxy-buta-1,3-diene 1) have been investigated. The antibody shows high selectivity for acetoxybutadiene which it hydrolyzes to the corresponding dienol, the major diene component of the cycloaddn. reactions obsd. However, it tolerates a range of N-alkylmaleimides. The stereochem. course of cycloaddn. is shown to produce a significant enantiomeric excess of the 3aR,4S,7aR-endo-diastereoisomer by anal. with Mosher's ester derivs. This study also revealed that H11 is capable of slowly catalyzing the hydrolysis of N-alkylmaleimide substrates. The implications for the mechanism of action of H11 are discussed. [on SciFinder(R)]

KW - antibody H11

KW - acetoxybutadiene

KW - Mosher's ester

KW - pure and applied chemistry

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

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

M3 - Article

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

Abstract

Keywords

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