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Updated: Jul 2, 2026
Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
Strategies for the solid-phase diversification of poly-L-proline-type II peptide mimic scaffolds and peptide
Stevenson Flemer1, Alexander Wurthmann, Ahmed Mamai
1Department of Chemistry, University of Vermont, Burlington, Vermont 05405, USA.
Abstract:
A strategy for the solid-phase diversification of PPII mimic scaffolds through guanidinylation is presented. The approach involves the synthesis N-Pmc-N'-alkyl thioureas as diversification reagents. Analogues of Fmoc-Orn(Mtt)-OH can be incorporated into a growing peptide chain on Wang resin. Side chain deprotection with 1% TFA/CH2Cl2 followed by EDCI-mediated reaction of N-Pmc-N'-alkyl thioureas with the side chain amine affords arginine analogues with modified guanidine head groups. The scope, limitations, and incidental chemistry are discussed.
