Some reactions of N-Ethylmaleimide

被引:306
作者
Smyth, Derek G. [1 ]
Nagamatsu, Atsuo [1 ]
Fruton, Joseph S. [1 ]
机构
[1] Yale Univ, Dept Biochem, New Haven, CT 06520 USA
关键词
D O I
10.1021/ja01502a039
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reactions of N-ethylmaleimide (NEM) with the amino group of peptides, with imidazole and with cysteine have been investigated. With the first two classes of compound, an IN-acylation reaction appears to occur, followed in the case of imidazole by a catalytic polymerization of NEM. With cysteine, reaction proceeds through addition of the thiol to the olefinic bond of NEM; in alkaline solution, the cysteine adduct undergoes all intramolecular transamidation reaction to form a thiazane derivative.
引用
收藏
页码:4600 / 4604
页数:5
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