Synthesis of a family of cyclic peptide-based anion receptors†
Stephen J. Butler,Katrina A. Jolliffe
Organic & Biomolecular Chemistry Pub Date : 03/23/2011 00:00:00 , DOI:10.1039/C0OB01072C
Abstract

We report here the design and synthesis of a family of novel backbone modified cyclic peptides, bearing dipicolylamine side chains for metal complexation and subsequent anion binding studies. Two approaches to the cyclic peptides were investigated. Initially, a stepwise approach was employed, involving solid-phase assembly of oxazole-based building blocks, followed by solution-phase macrolactamisation of the resulting linear precursor. The alternative strategy involved the formation of linear bisoxazole fragments in solution-phase, followed by a cyclodimerisation reaction. The zinc(II) complexes of these receptors bind selectively to di- and tri-phosphate ions over hydrogenphosphate.

Graphical abstract: Synthesis of a family of cyclic peptide-based anion receptors