1044253-23-7Relevant academic research and scientific papers
Backbone amide linker strategy for the synthesis of 1,4-triazole-containing cyclic tetra- and pentapeptides
Springer, Jasper,De Cuba, Kimberly R.,Calvet-Vitale, Sandrine,Geenevasen, Jan A. J.,Hermkens, Pedro H. H.,Hiemstra, Henk,Van Maarseveen, Jan H.
experimental part, p. 2592 - 2600 (2009/04/05)
A backbone amide linker strategy was chosen for the solid-phase synthesis of triazole-containing cyclic tetra- and pentapeptides. An alkyne-substituted linker derived from 4-hydroxy-2-methoxybenzaldehyde was elongated by using standard Fmoc-based solid phase chemistry and terminated by coupling of an azido acid. In solution, the peptides were cyclized by a Cu I-catalyzed azide-alkyne cycloaddition reaction. The solid-supported synthesized linear peptides had to be cleaved prior to cyclization. As an example of cyclic tetrapeptides, a triazole analog of cyclo-[Pro-Val-Pro-Tyr] (2) was prepared by the solid-phase/solution-phase method. For the cyclic pentapeptides, segetalin B (3) was chosen as a model compound to show the applicability of this method. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
