title: Strategies for the solid-phase diversification of poly-L-proline-type II peptide mimic scaffolds and peptide scaffolds through guanidinylation.
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.
authors.affiliation: Department of Chemistry, University of Vermont, Burlington, Vermont 05405, USA.
authors.forename: Stevenson
authors.initials: S
authors.lastname: Flemer
authors.forename: Alexander
authors.initials: A
authors.lastname: Wurthmann
authors.forename: Ahmed
authors.initials: A
authors.lastname: Mamai
authors.forename: José S
authors.initials: JS
authors.lastname: Madalengoitia