947748-55-2Relevant academic research and scientific papers
Strategies for the solid-phase diversification of poly-L-proline-type II peptide mimic scaffolds and peptide scaffolds through guanidinylation
Flemer, Stevenson,Wurthmann, Alexander,Mamai, Ahmed,Madalengoitia, Jose S.
, p. 7593 - 7602 (2008/12/22)
(Chemical Equation Presented) 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.
Synthetic routes to N-Pmc-N′,N″-disubstituted guanidines via EDCI-mediated guanylation of amines with N-Pmc-N′-substituted thioureas
Flemer Jr., Stevenson,Madalengoitia, Jose S.
, p. 1848 - 1860 (2008/02/10)
An overview of the facile and high-yielding EDCI-mediated reaction of amines with N-Pmc-N′-alkyl thioureas to afford guanidines is presented, in which the general scope and limitations of the reaction are probed. It was found that the N-sulfonyl-N′-substi
