Issue 36, 2015
From the journal:

Organic & Biomolecular Chemistry

Oxidative α,ω-diyne coupling as an approach towards novel peptidic macrocycles†

S. Verlinden,a   N. Geudens,b   J. C. Martins,b   D. Tourwé,a   S. Balleta  and  G. Verniest*a  

* Corresponding authors

a 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
E-mail: gvernies@vub.ac.be

b NMR and Structure Analysis Unit, Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, 9000 Ghent, Belgium

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.

Graphical abstract: Oxidative α,ω-diyne coupling as an approach towards novel peptidic macrocycles

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Article information

DOI
https://doi.org/10.1039/C5OB01153A
Article type
Paper
Submitted
08 Jun 2015
Accepted
20 Jul 2015
First published
06 Aug 2015

Org. Biomol. Chem., 2015,13, 9398-9404

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Oxidative α,ω-diyne coupling as an approach towards novel peptidic macrocycles

S. Verlinden, N. Geudens, J. C. Martins, D. Tourwé, S. Ballet and G. Verniest, Org. Biomol. Chem., 2015, 13, 9398 DOI: 10.1039/C5OB01153A

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