Sulfonamide bearing oligonucleotides: simple synthesis and efficient RNA recognition

Bioorganic & Medicinal Chemistry
Pawan KumarPawan K Sharma

Abstract

Four pyrimidine nucleosides wherein a benzensulfonamide group is linked to the C-5 position of the uracil nucleobase through a triazolyl or an alkynyl linker were prepared by Cu(I)-assisted azide-alkyne cycloadditions (CuAAC) or Sonogashira reactions, respectively, and incorporated into oligonucleotides. Efficient π-π-stacking between two or more phenyltriazoles in the major groove was found to increase the thermal stability of a DNA:RNA duplex significantly. On the other hand, the alkynyl group was not as efficient in stacking as the triazolyl group. No effect of positional orientation of the sulfonamide group on the stacking efficiency was observed, and the most stable DNA:RNA duplex contained four consecutive sulfonamide substituted phenyltriazole moieties in the major groove.

References

Dec 18, 2003·Drug Discovery Today·Hartmuth C Kolb, K Barry Sharpless
Feb 21, 2008·Chembiochem : a European Journal of Chemical Biology·Renatus W SinkeldamYitzhak Tor

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Citations

Jul 20, 2016·Journal of Medicinal Chemistry·W Brad Wan, Punit P Seth
Jun 9, 2015·Organic & Biomolecular Chemistry·Michael DalagerPawan K Sharma
Oct 30, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tim EfthymiouJean-Paul Desaulniers
Aug 11, 2017·ChemistryOpen·Paz TrilloHans Adolfsson
Jul 2, 2021·Beilstein Journal of Organic Chemistry·Vineet VermaAshok K Prasad
Oct 9, 2012·The Journal of Organic Chemistry·Pawan KumarPoul Nielsen

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