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Use of trifluoromethylated nucleotide analogs as 19F‐NMR probes of DNA structure
Author(s) -
Wright Justin,
Stoub Darren
Publication year - 2010
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.24.1_supplement.652.1
Subject(s) - guanosine , trifluoromethyl , chemistry , nucleic acid , dna , fluorine 19 nmr , nucleotide , stereochemistry , fluorine , adenosine , nuclear magnetic resonance spectroscopy , biochemistry , organic chemistry , alkyl , gene
The dynamics of conformational changes in DNA and RNA are important in many biological processes. Fluorine NMR has been shown to be a valuable structural tool for studying RNA and DNA and their interactions with other compounds. Unfortunately, many of the fluorinated nucleosides utilized are either unstable, expensive, or change nucleic acid structure. We report our efforts toward the synthesis of the phosphoramidites of 8‐aza‐7‐deaza‐7‐trifluoromethyl guanosine, 8‐aza‐7‐deaza‐7‐trifluoromethyl adenosine, 8‐trifluoromethyl guanosine and 8‐trifluoromethyl adenosine ribonucleosides. We also report our efforts in incorporating the analogs into DNA, the impact of the analogs on DNA stability using thermal denaturation, and our initial NMR experimental results.