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Open AccessArticle

A Dynamic Combinatorial Approach for Identifying Side Groups that Stabilize DNA-Templated Supramolecular Self-Assemblies

Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS-Université de Montpellier, ENSCM, Ecole Nationale Supérieure de Chimie de Montpellier, 8 Rue de l'Ecole Normale, Montpellier Cedex 5 34296, France
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Academic Editor: John George Hardy
Int. J. Mol. Sci. 2015, 16(2), 3609-3625; https://doi.org/10.3390/ijms16023609
Received: 5 January 2015 / Revised: 16 January 2015 / Accepted: 23 January 2015 / Published: 6 February 2015
(This article belongs to the Special Issue Supramolecular Interactions)
DNA-templated self-assembly is an emerging strategy for generating functional supramolecular systems, which requires the identification of potent multi-point binding ligands. In this line, we recently showed that bis-functionalized guanidinium compounds can interact with ssDNA and generate a supramolecular complex through the recognition of the phosphodiester backbone of DNA. In order to probe the importance of secondary interactions and to identify side groups that stabilize these DNA-templated self-assemblies, we report herein the implementation of a dynamic combinatorial approach. We used an in situ fragment assembly process based on reductive amination and tested various side groups, including amino acids. The results reveal that aromatic and cationic side groups participate in secondary supramolecular interactions that stabilize the complexes formed with ssDNA. View Full-Text
Keywords: dynamic combinatorial chemistry; dynamic covalent chemistry; DNA-templated self-assembly; supramolecular interactions dynamic combinatorial chemistry; dynamic covalent chemistry; DNA-templated self-assembly; supramolecular interactions
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Paolantoni, D.; Cantel, S.; Dumy, P.; Ulrich, S. A Dynamic Combinatorial Approach for Identifying Side Groups that Stabilize DNA-Templated Supramolecular Self-Assemblies. Int. J. Mol. Sci. 2015, 16, 3609-3625.

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