A 1H and 13C nuclear magnetic resonance study of nucleosides with methylated pyrimidine bases
- 15 December 1982
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 60 (24) , 3026-3032
- https://doi.org/10.1139/v82-433
Abstract
Alkylated pyrimidine bases are of interest from the viewpoint of mutagenesis and carcinogenesis. 1H nuclear magnetic resonance data are presented for a series of ribosides and arabinosides alkylated at the O2,O4, N3, and C5 positions of the pyrimidine base. The data provide information about the stereochemical effects of base methylation. The J(5—6) proton coupling constants show that O-alkylation leads to a decrease in the π-bond order of the C5—C6 bond. The 13C chemical shifts are related to the tautomeric changes effected by O-alkylation.Keywords
This publication has 9 references indexed in Scilit:
- Advanced nuclear magnetic resonance lanthanide probe analyses of short-range conformational interrelations controlling ribonucleic acid structuresBiochemistry, 1981
- Influence of substituents at the 5 position on the structure of uridineJournal of the American Chemical Society, 1980
- A 13Cmr study of 2′-deoxynucleotides in the syn and anti conformationCanadian Journal of Chemistry, 1980
- 1H nuclear magnetic resonance study of 2,2′-anhydro-O2-β-D-arabinosyluracil. Four- and five-bond coupling constants in the sugar moietyCanadian Journal of Chemistry, 1979
- Preparation and template activities of polynucleotides containing O2- and O4-alkyluridine.Proceedings of the National Academy of Sciences, 1978
- Carbon-13 nuclear magnetic resonance spectra of N-, O-, and S-methylated uracil and thiouracil derivativesCanadian Journal of Chemistry, 1978
- Phosphorus-31 Fourier transform nuclear magnetic resonance study of mononucleotides and dinucleotides. 2. Coupling constantsBiochemistry, 1976
- Taulomerism and Electronic Structure of Biological PyrimidinesPublished by Elsevier ,1975
- Infrared spectra and tautomeric structure in D2O solution of some pyrimidine nucleosides and nucleotidesBiochimica et Biophysica Acta, 1956