title: Oxidative α,ω-diyne coupling as an approach towards novel peptidic macrocycles.
abstract: The Glaser-Hay diyne coupling proved to be an efficient cyclisation approach towards diyne containing peptidic macrocycles. A variety of tetrapeptide-based macrocyclic 1,3-diynes were obtained from O-propargylated serine or tyrosine residues using Cu(OAc)2·H2O and NiCl2 under an O2-atmosphere. The effect of the linear 1,3-diyne on peptide conformations was studied by NMR and compared with a macrocycle bearing a saturated linker.
authors.affiliation: Research Group of Organic Chemistry, Department of Chemistry and Department of Bio-engineering Sciences, Faculty of Science and Bio-engineering Sciences, Vrije Universiteit Brussel, Pleinlaan (VUB) 2, B-1050 Brussels, Belgium. gvernies@vub.ac.be.
authors.forename: S
authors.initials: S
authors.lastname: Verlinden
authors.forename: N
authors.initials: N
authors.lastname: Geudens
authors.forename: J C
authors.initials: JC
authors.lastname: Martins
authors.forename: D
authors.initials: D
authors.lastname: Tourwé
authors.forename: S
authors.initials: S
authors.lastname: Ballet
authors.forename: G
authors.initials: G
authors.lastname: Verniest
mesh_terms: D003500:Cyclization; D053280:Diynes / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D053280:Diynes; D047028:Macrocyclic Compounds; D010455:Peptides