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Nucleic Acids Research, 1984, Vol. 12, No. 4 2205-2223
© 1984

CHEMISTRY

Comparative structural analysis of cytidine, ethenocylidine and their protonated salts III. 1H, 13C and 15NNMR studies at natural isotope abundance

Lech Kozerski+, Hanna Sierzputowska-Gracz, Wiodzimierz Krzosiak, Maria Bratek-Wiewiórowska§ and Maciej Wiewiórowski*

Institute of Bioorganik Chemistry, Polish Academy of Sciences 61-704 Poznan +Institute of Organic Chemistry, Polish Academy of Sciences 00-961 Warszawa §Department of Crystallography, Institute of Chemistry, Adam Mickiewicz University 60-780 Poznan, Poland

*To whom correspondence should be addressed

Received October 26, 1983. Revised January 12, 1984. Accepted January 26, 1984.

The 1H, 13C, 15N NMR spectra of cytidine /Cyd/, ethenocytidine /{varepsilon}Cyd/ and their hydrochlorides /Cyd HC1/ and /{varepsilon}Cyd.HCl/ have been analysod to compare structural differences observed in solution with those existing in the crystalline state. The effects of ethenobridging and protonation of the hetero-aromatic base on the intramolecular stereochemistry, intormolecui.ar interactions and electronic structure of the whole molocule 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' -O...H-6-c hydrogen bond, unambiguous assignment of the site of protonation, the mechanism of the 5C-H deuterium exchange in Cyd HCl, and the intermolecular interactions in solution.


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