ISSN:
0749-1581
Keywords:
1H NMR
;
2′-Deoxyribonucleosides
;
Prochiral C-5′ proton assignment
;
Rotamer populations
;
Hydroxymethyl rotamers
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
2′-Deoxyadenosine, 2′-deoxycytidine, 2′-deoxyguanosine and 2′-deoxyuridine were prepared with stereoselective deuteriation at C-5′ and used to assign the prochiral C-5′ protons in 300 MHz 1H NMR spectra obtained in 2H2O. In all cases, the more shielded C-5′ proton was found to be the pro-R proton. From these assignments, C-4′-C-5′ rotamer populations were determined using three previously published methods based on the spin couplings, 3J(H-4′,H-5′R) and 3J(H-4′,H-5′S), and the errors associated with these methods were assessed. The effects of base structure, furanose and N-glycoside bond conformation on the relative populations of hydroxymethyl rotamers in nucleosides are discussed.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260280409
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