ISSN:
0749-1581
Keywords:
1H NMR
;
19F NMR
;
Conformational analysis
;
6-Deoxy-6-fluoro-D-glucose
;
D-Glucopyranose
;
Rotamer populations
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The conformation of D-glucopyranose and 6-deoxy-6-fluoro-D-glucose (6DFG) in solution, as determined by 1H and 19F NMR, is reviewed. The 1H NMR spectra of α- and β-methyl D-glucopyranosides and 6DFG in methanol, acetone, DMSO, and aqueous solution were acquired and fully analysed. A 19F NMR spectrum of the methanol 6DFG solution, together with a 1H COSY spectrum of α-6DFG in methanol, were recorded. Accurate analyses of the ABC and ABCX spectra produced by the —CHCH2OH and —CHCH2F moieities, respectively, were performed, and from the vicinal J(H-5,H-6) coupling constants the populations of the three possible staggered rotamers about the C-5—C-6 bond were calculated. The rotamer in which F is antiperiplanar to the ring O is particularly disfavoured, whereas the rotamer with F antiperiplanar to H-5 is most favoured. This general trend was seen for both pyranose anomers in all four solvents.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260301313
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