Chiral hydroxymethyl groups: 1H NMR assignments of the prochiral C??5′ protons of 2′??deoxyribonucleosides

PC Kline, AS Serianni

Index: Kline, Paul C.; Serianni, Anthony S. Magnetic Resonance in Chemistry, 1990 , vol. 28, p. 324 - 330

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Citation Number: 19

Abstract

Abstract 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 1 H NMR spectra obtained in 2 H 2 O. 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 ...