Tuning the properties of a cyclic RGD-containing tetrapeptide through backbone fluorination

Catherine Au; Christina Gonzalez; Yun Cheuk Leung; Flora Mansour; Johny Trinh; Zhiyong Wang; Xiang-Guo Hu; Renate Griffith; Eddy Pasquier; Luke Hunter

doi:10.1039/C8OB02679C

Tuning the properties of a cyclic RGD-containing tetrapeptide through backbone fluorination†

Catherine Au,

‡^a Christina Gonzalez,‡^a Yun Cheuk Leung,‡^a Flora Mansour,‡^a Johny Trinh,‡^a Zhiyong Wang,‡^a Xiang-Guo Hu,

§^a Renate Griffith,^b Eddy Pasquier

^c and Luke Hunter

*^ad

Author affiliations

* Corresponding authors

^a School of Chemistry, UNSW Sydney, NSW 2052, Australia
E-mail: l.hunter@unsw.edu.au

^b School of Medical Sciences, UNSW Sydney, NSW 2052, Australia

^c CNRS, INSERM, Aix-Marseille University, Institut Paoli-Calmettes, Centre de Recherche en Cancérologie de Marseille, Marseille, France

^d School of Chemistry, The University of Sydney, NSW 2006, Australia

Abstract

Stereoselective fluorination is investigated as a method for modulating the properties of a cyclic RGD-containing tetrapeptide. Three key outcomes of fluorination are assessed: (i) the effect on peptide cyclisation efficiency; (ii) the ability to fine-tune the molecular conformation; and (iii) the effect on the cyclic peptides’ biological activity. Fluorination is found to exert pronounced effects against all three criteria.

This article is part of the themed collection: Fluorine Chemistry

Organic & Biomolecular Chemistry

Tuning the properties of a cyclic RGD-containing tetrapeptide through backbone fluorination†

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Tuning the properties of a cyclic RGD-containing tetrapeptide through backbone fluorination

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