Synthesis, duplex-forming properties, and enzymatic resistance of oligonucleotides containing <i>N</i> -acylsulfonamide linkages

We report the synthesis of (2-(<i>N</i>-acetylsulfamoyl)ethyl)carbamate (NAC)-linked thymidine dinucleotide <i>via</i> the sulfo-click reaction and its incorporation into DNA oligonucleotides. Thermal denaturation studies indicate modest destabilization at duplex ends (∼1 °C) and stronger effects in the middle (∼7 °C), while the NAC linkage provides complete resistance to nucleases.

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Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob01382h
Primary Topic
DNA and Nucleic Acid Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Synthesis, duplex-forming properties, and enzymatic resistance of oligonucleotides containing N -acylsulfonamide linkages

Romain Amador, Michaël Smietana, Guillaume Clavé, Carine Baraguey
Organic & Biomolecular Chemistry
DNA and Nucleic Acid Chemistry
article

Synthesis, duplex-forming properties, and enzymatic resistance of oligonucleotides containing N -acylsulfonamide linkages

Romain Amador, Michaël Smietana, Guillaume Clavé, Carine Baraguey
article en

Abstract

We report the synthesis of (2-(<i>N</i>-acetylsulfamoyl)ethyl)carbamate (NAC)-linked thymidine dinucleotide <i>via</i> the sulfo-click reaction and its incorporation into DNA oligonucleotides. Thermal denaturation studies indicate modest destabilization at duplex ends (∼1 °C) and stronger effects in the middle (∼7 °C), while the NAC linkage provides complete resistance to nucleases.

Organic & Biomolecular ChemistryVol. 23(42)
École Nationale Supérieure de Chimie de Montpellier (FR), Centre National de la Recherche Scientifique (FR), Université de Montpellier (FR), Institut des Biomolécules Max Mousseron (FR)
Agence Nationale de la Recherche
Openalex Percentile: Top 76%
DNA and Nucleic Acid Chemistry
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Synthesis, duplex-forming properties, and enzymatic resistance of oligonucleotides containing <i>N</i> -acylsulfonamide linkages — Romain Amador, Michaël Smietana, et al. · Organic & Biomolecular Chemistry (2025) | TGRS Research Map | TGRS