Issue 32, 2020

Access to a stabilized i-motif DNA structure through four successive ligation reactions on a cyclopeptide scaffold

Abstract

i-Motifs are largely underexplored tetraplex nucleic acid structures which have been suggested to perform essential biological functions and might constitute future therapeutic targets. i-Motifs generally require acidic conditions to fold in vitro, a particularity which significantly complicates the use of native i-motif forming sequences for interaction studies with potential ligands and biological components (e.g. proteins). In this context, we report herein on the assembly of a peptide–DNA conjugate capable of folding at room temperature into a stable i-motif structure at neutral pH. To achieve the controlled assembly of the i-motif forming conjugate, we developed a new synthetic pathway of four successive orthogonal ligation reactions between bifunctional C-rich DNA strands and a tetrafunctional cyclopeptide scaffold.

Graphical abstract: Access to a stabilized i-motif DNA structure through four successive ligation reactions on a cyclopeptide scaffold

Supplementary files

Article information

Article type
Paper
Submitted
25 Jun 2020
Accepted
23 Jul 2020
First published
31 Jul 2020
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2020,18, 6394-6406

Access to a stabilized i-motif DNA structure through four successive ligation reactions on a cyclopeptide scaffold

A. Devaux, L. Bonnat, T. Lavergne and E. Defrancq, Org. Biomol. Chem., 2020, 18, 6394 DOI: 10.1039/D0OB01311K

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