Issue 9, 2011

Synthesis of a family of cyclic peptide-based anion receptors

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

Supplementary files

Article information

Article type
Paper
Submitted
24 Nov 2010
Accepted
16 Feb 2011
First published
23 Mar 2011

Org. Biomol. Chem., 2011,9, 3471-3483

Synthesis of a family of cyclic peptide-based anion receptors

S. J. Butler and K. A. Jolliffe, Org. Biomol. Chem., 2011, 9, 3471 DOI: 10.1039/C0OB01072C

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