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Issue 26, 2019
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Convertible and conformationally constrained nucleic acids (C2NAs)

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Abstract

We introduce the concept of Convertible and Constrained Nucleic Acids (C2NAs). By means of the synthesis of a stereocontrolled N-propargyl dioxo-1,3,2-oxaza-phosphorinane as an internucleotidic linkage, the torsional angles α and β can adopt either the canonical (g, t) set of values able to increase DNA duplex stability or the non-canonical (g+, t) set that stabilized the hairpin structure when installed within the loop moiety. With an appended propargyl function on the nitrogen atom of the six-membered ring, the copper catalysed Huisgen's cycloaddition (CuAAC click chemistry) allows for the introduction of new functionalities at any location on the nucleic acid chain while maintaining the properties brought by the geometrical constraint and the neutral internucleotidic linkage.

Graphical abstract: Convertible and conformationally constrained nucleic acids (C2NAs)

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Article information


Submitted
16 May 2019
Accepted
05 Jun 2019
First published
05 Jun 2019

Org. Biomol. Chem., 2019,17, 6386-6397
Article type
Paper

Convertible and conformationally constrained nucleic acids (C2NAs)

J. Escudier, C. Payrastre, B. Gerland and N. Tarrat, Org. Biomol. Chem., 2019, 17, 6386
DOI: 10.1039/C9OB01150A

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