Open AccessComparative structural analysis of cytidine, ethenocylidine and their protonated salts III.1H,13C and15NNMR studies at natural isotope abundance
Author(s) -
Lech Kozerski,
Hanna Sierzputowska-Gracz,
Wiodzimierz Krźosiak,
M. D. Bratek-Wiewiórowska,
M. Wiewiórowski
Publication year - 1984
Publication title -
nucleic acids research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 9.008
H-Index - 537
eISSN - 1362-4954
pISSN - 0305-1048
DOI - 10.1093/nar/12.4.2205
Subject(s) - protonation , intramolecular force , intermolecular force , hydrogen bond , kinetic isotope effect , cytidine , deuterium , molecule , crystallography , nuclear magnetic resonance spectroscopy , stereochemistry , nmr spectra database , chemistry , spectral line , organic chemistry , physics , ion , quantum mechanics , enzyme , astronomy
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.