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 intermediate. The Young and Anteunis tests show that the degree of epimerization is very low in methylene chloride and acetonitrile.
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