Synthesis of new C-5-triazolyl-functionalized thymidine analogs and their ability to engage in aromatic stacking in DNA : DNA and DNA : RNA duplexes

By Mick Hornum, Alevtina Djukina, Ann-Katrin Sassnau, Poul Nielsen

July 28, 2017

  • Year

  • Technique

  • Industry

Title

Synthesis of new C-5-triazolyl-functionalized thymidine analogs and their ability to engage in aromatic stacking in DNA : DNA and DNA : RNA duplexes

Author

Mick Hornum, Alevtina Djukina, Ann-Katrin Sassnau, Poul Nielsen

Year

2016

Journal

Organic and Biomolecular Chemistry

Abstract

1-Phenyl-1,2,3-triazole scaffolds on the 5-position of pyrimidine nucleosides have previously shown to enhance nuclease stability and increase the duplex thermal stability (Tm) by engaging in duplex stacking interactions. In this study, we have introduced two new derivatives of this scaffold in DNA : DNA and DNA : RNA duplexes in order to explore the thermal effects of (1) using a 1,5-triazole instead of the usual 1,4-triazole, and (2) replacing the apolar phenyl substituent with a polar uracil-5-yl substituent.

Full Article

http://pubs.rsc.org/en/content/articlelanding/2016/ob/c6ob00609d

Instrument

J-715

Keywords

Circular dichroism, Secondary structure, Biochemistry