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Chiral hydroxymethyl groups: 1 H NMR assignments of the prochiral C‐5′ protons of ribonucleosides
Author(s) -
Kline Paul C.,
Serianni Anthony S.
Publication year - 1988
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.1260260207
Subject(s) - chemistry , conformational isomerism , guanosine , hydroxymethyl , proton , stereoselectivity , ring (chemistry) , stereochemistry , proton nmr , uridine , cytidine , nmr spectra database , alkane stereochemistry , nuclear magnetic resonance spectroscopy , spectral line , crystallography , molecule , organic chemistry , crystal structure , catalysis , rna , biochemistry , physics , quantum mechanics , astronomy , gene , enzyme
Adenosine, cytidine, guanosine and uridine were prepared with stereoselective deuteriation at C‐5′ and used to assign the prochiral C‐5′ protons in 300 MHz 1 H NMR spectra. 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 have been estimated, and some discussion of the errors associated with these calculations is given. The relative populations of rotamers in ribonucleosides were found to be affected by structure at C‐1, ring conformation and possibly solution pH.