Solid-phase synthesis of peptide thioesters with self-purification

Abstract

Separating the wheat from the chaff: A cyclization-thiolysis sequence adds a new property to sulfonamide safety-catch resins. Activation of the sulfonamide is used to introduce a carboxy group for subsequent macrocyclization. Truncation products are noncyclic and hence washed away following thiolytic ring opening. Only the full-length peptide thioesters are detached, usually in pure form, in the final step. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.