Peptide−Small Molecule Hybrids via Orthogonal Deprotection−Chemoselective Conjugation to Cysteine-Anchored Scaffolds. A Model Study

Abstract

The feasibility of an orthogonal deprotection-conjugation protocol, holding the promise of libraries of functionally diverse chemical probes attached to cysteine-anchored peptide scaffolds, has been explored with a model system. The necessary tools for assembly of the hybrid libraries have been prepared and the tandem procedure optimized. S-alkylation and S-sulfenylation are featured as the chemoselective ligation reactions. [reaction: see text]