A1 Journal article – refereed

4 '-C-[(4-Trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine as a Sensitive F-19 NMR Sensor for the Detection of Oligonucleotide Secondary Structures




List of Authors: Lotta Granqvist, Pasi Virta

Publisher: AMER CHEMICAL SOC

Publication year: 2014

Journal: Journal of Organic Chemistry

Journal name in source: JOURNAL OF ORGANIC CHEMISTRY

Journal acronym: J ORG CHEM

Volume number: 79

Issue number: 8

Number of pages: 8

ISSN: 0022-3263

DOI: http://dx.doi.org/10.1021/jo500326j


Abstract

4'-C-[(4-Trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl]thymidine was synthesized and incorporated as a phosphoramidite into oligonucleotide sequences. Its applicability as a sensor for the F-19 NMR spectroscopic detection of DNA and RNA secondary structures was demonstrated. On DNA, the F-19 NMR measurements were focused on monitoring of duplex-triplex conversion, for which this fluorine-labeled 2'-deoxynucleoside proved to be a powerful sensor. This sensor seemingly favors DNA, but its behavior in the RNA environment also turned out to be informative. As a demonstration, invasion of a 2'-O-methyl oligoribonucleotide into an RNA hairpin model (HIV-1 TAR) was monitored by F-19 NMR spectroscopy. According to the thermal denaturation studies by UV spectroscopy, the effect of the 4'-C-(4-trifluoromethyl-1H-1,2,3-triazol-1-yl)methyl moiety on the stability of these DNA and RNA models was marginal.



Last updated on 2021-24-06 at 09:20