Backbone amide linker strategy for the synthesis of 1,4-triazole-containing cyclic tetra- and pentapeptides

Autor:	Kimberly R. de Cuba, Sandrine Calvet-Vitale, Jan A. J. Geenevasen, Jasper Springer, Henk Hiemstra, Pedro H. H. Hermkens, Jan H. van Maarseveen
Přispěvatelé:	Synthetic Organic Chemistry (HIMS, FNWI)
Rok vydání:	2008
Předmět:	chemistry.chemical_classification biology Chemistry Stereochemistry Organic Chemistry Triazole biology.organism_classification Combinatorial chemistry Cycloaddition Cyclic peptide chemistry.chemical_compound Amide Click chemistry Tetra Segetalin B Physical and Theoretical Chemistry Linker
Zdroj:	European Journal of Organic Chemistry, 2592-2600. Wiley-VCH Verlag ISSUE=15;STARTPAGE=2592;ENDPAGE=2600;ISSN=1434-193X;TITLE=European Journal of Organic Chemistry
ISSN:	1434-193X
Popis:	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-1-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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1726c42044a6092236ce404429d55910 https://hdl.handle.net/11245/1.294294 Zobrazit plný text záznamu Plný text