Direct Fmoc-chemistry-based solid-phase synthesis of peptidyl thioesters

Abstract

Attachment of a growing peptide chain to a glycylaminomethyl resin via a thioglycinamide bond is compatible with Fmoc-chemistry solid-phase peptide synthesis. Subsequent S-alkylation of the thioamide gives a thioimide that, on treatment with aqueous trifluoroacetic acid, releases the peptide from the resin in the form of a C-terminal thioester.