Journal
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
Volume 40, Issue 2, Pages 212-221Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/15257770.2020.1861288
Keywords
NMR; H-1-NMR; nucleoside conformation; single-crystal X-ray crystallography; thermodynamics cycle
Categories
Funding
- National Natural Science Foundation of China [81373462, 8151101082]
- Basal Research Fund of the National Health Commission Key Laboratory of Birth Defect Prevention [JBKY2019011]
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The conformational features of drugs are crucial for their biological activity. This report investigated the solid-state and solution conformations of nucleosides, showing different preferences and stability. The results highlight the importance of conformational analysis for understanding drug behavior in different environments.
The conformational features of drugs are important with respect to their biological activity. In this report, we confirmed the solid-state conformation of 1-(4 '-azido-2 '-deoxy-2 '-fluoro-beta-d-arabinofuranosyl) cytosine using single-crystal X-ray crystallography and the conformations of three 2 '-deoxy-2 '-fluoro-4 '-substituted nucleosides in solution using Altona-Haasnoot's equations and Nuclear Overhauser effect spectroscopy (NOESY). Furthermore, we compared the preferred solid-state and solution conformation of these nucleosides with thermodynamics cycles to obtain more evidence of their conformations. The results showed 1-(4 '-azido-2 '-deoxy-2 '-fluoro-beta-d-arabinofuranosyl) cytosine was south type conformation (C-3 '-exo) in solid-state and three 4 '-substituted nucleosides were north type conformations (C-3 '-endo) in solution. The north type conformations in solution indicated these compounds were steady to acidic and enzymatic N-glycolysis.
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