Comparative structural analysis of cytidine, ethenocytidine and their protonated salts III. 1H, 13C and 15N NMR studies at natural isotope abundance.
AUTOR(ES)
Kozerski, L
RESUMO
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.
ACESSO AO ARTIGO
http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=318652Documentos Relacionados
- Comparative structural analysis of 1-methyladenosine, 7-methylguanosine, ethenoadenosine and their protonated salts IV: 1H, 13C, and 15N NMR studies at natural isotope abundance.
- Comparative structural analysis of cytidine, ethenocytidine and their protonated salts. II. IR spectral studies.
- Comparative structural analysis of cytidine, ethenocytidine, and their protonated salts. I. Crystal and molecular structure of ethenocytidine.
- Proton-coupled 15N NMR spectra of neutral and protonated ethenoadenosine and ethenocytidine.
- Preparation of 13C and 15N labelled RNAs for heteronuclear multi-dimensional NMR studies.