Reactions of N-ethylmaleimide with peptides and amino acids

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Abstract
The rates of reaction of N-ethyl-maleimide with the [alpha]-amino groups of three peptides are reported. Some observations are presented on the isomerism of the addition products of N-ethylmaleimide with thiol compounds. A detailed analysis of the products of hydrolysis of these derivatives was performed. A method for the determination of the degree of reaction of N-ethylmaleimide with the thiol groups of proteins is proposed, together with a means of assessing the specificity of the reaction. The results are of significance in the use of N-ethylmaleimide as a reagent for the introduction of chemical modifications in proteins.