Tetrahedron Letters

A low-epimerizing peptide coupling reagent based on the rearrangement of a carboxylic-sulfonic mixed anhydride

D Cabaret, M Wakselman

文献索引：Cabaret, Daniel; Wakselman, Michel Tetrahedron Letters, 1994 , vol. 35, # 51 p. 9561 - 9564

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被引用次数: 9

摘要

Abstract A series of peptides has been prepared using an o-hydroxybenzenesulfonyl chloride as the condensation reagent. Experimentally, the coupling is a one pot two-steps reaction: formation and aminolysis of a substituted aryl ester. The first step occurs by an elimination-addition reaction involving a sulfoquinone intermediate, followed by an efficient six-membered acyl transfer reaction in the phenolic carboxylic-sulfonic mixed anhydride ...