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Chiral hydroxymethyl groups: 1 H NMR assignments of the prochiral C‐5′ protons of 2′‐deoxyribonucleosides
Author(s) -
Kline Paul C.,
Serianni Anthony S.
Publication year - 1990
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260280409
Subject(s) - chemistry , furanose , conformational isomerism , deoxyribonucleosides , hydroxymethyl , stereochemistry , proton nmr , deoxyadenosine , stereoselectivity , proton , glycal , molecule , dna , ring (chemistry) , organic chemistry , catalysis , biochemistry , physics , quantum mechanics
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 methods based on the spin couplings, 3 J (H‐4′,H‐5′ R ) and 3 J (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.