Abstract
The 1H, 13C, 15N NMR spectra of cytidine /Cyd/, ethenocytidine /epsilon Cyd/ and their hydrochlorides /Cyd X HC1/ and /epsilon Cyd X HC1/ have been analysed to compare structural differences observed in solution with those existing in the crystalline state. The effects of ethenobridging and protonation of the hertero-aromatic base on the intramolecular stereochemistry, intermolecular interactions and electronic structure of the whole molecule are discussed on the basis of the NMR studies in DMSO solutions. Particular interest is devoted to the discussion of the conformation of the ribose ring, the presence of the intramolecular C-5'-0...H-6-C hydrogen bond, unambiguous assignment of the site of protonation, the mechanism of the 5C-H deuterium exchange in Cyd X HC1, and the intermolecular interactions in solution.
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Selected References
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- Barrio J. R., Sattsangi P. D., Gruber B. A., Dammann L. G., Leonard N. J. Species responsible for the fluorescence of 3,N4-ethenocytidine. J Am Chem Soc. 1976 Nov 10;98(23):7408–7414. doi: 10.1021/ja00439a049. [DOI] [PubMed] [Google Scholar]
- Jaskólski M., Krzyzosiak W., Sierzputowska-Gracz H., Wiewiórowski M. Comparative structural analysis of cytidine, ethenocytidine, and their protonated salts. I. Crystal and molecular structure of ethenocytidine. Nucleic Acids Res. 1981 Oct 24;9(20):5423–5442. doi: 10.1093/nar/9.20.5423. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Krzyzosiak W., Jaskólski M., Sierzputowska-Gracz H., Wiewiórowski M. Comparative structural analysis of cytidine, ethenocytidine and their protonated salts. II. IR spectral studies. Nucleic Acids Res. 1982 Apr 24;10(8):2741–2753. doi: 10.1093/nar/10.8.2741. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Markowski V., Sullivan G. R., Roberts J. D. Nitrogen-15 nuclear magnetic resonance spectroscopy of some nucleosides and nucleotides. J Am Chem Soc. 1977 Feb 2;99(3):714–718. doi: 10.1021/ja00445a009. [DOI] [PubMed] [Google Scholar]
- Remin M., Shugar D. Conformational analysis of cytidine, 1-beta-D-(arabinofuranosyl)cytosine and their O'-methyl derivatives by proton magnetic resonance spectroscopy. J Am Chem Soc. 1973 Nov 28;95(24):8146–8156. doi: 10.1021/ja00805a031. [DOI] [PubMed] [Google Scholar]
- Reynolds W. F., Peat I. R., Freedman M. H., Lyerla J. R., Jr Determination of the tautomeric form of the imidazole ring of L-histidine in basic solution by carbon-13 magnetic resonance spectroscopy. J Am Chem Soc. 1973 Jan 24;95(2):328–331. doi: 10.1021/ja00783a006. [DOI] [PubMed] [Google Scholar]
- Shapiro R., Klein R. S. Reactions of cytosine derivatives with acidic buffer solutions. II. Studies on transamination, deamination, and deuterium exchange. Biochemistry. 1967 Nov;6(11):3576–3582. doi: 10.1021/bi00863a032. [DOI] [PubMed] [Google Scholar]