Carbon‐13 as a tool for the study of carbohydrate structures, conformations and interactions
- 1 January 1977
- journal article
- research article
- Published by Wiley in Journal of Supramolecular Structure
- Vol. 6 (4), 535-550
- https://doi.org/10.1002/jss.400060407
Abstract
The application of 13C-NMR spectroscopy to problems involving the structures and interactions of carbohydrates is described. Both 13C-enriched and natural abundance compounds were used and some advantages of the use of the stable isotope are described. Carbon-carbon and carbon-proton coupling constants obtained from 1-13 C enriched carbohydrates were employed in the assignment of their chemical shifts and to establish solution conformation. In all cases studied thus far, C-3 couples to C-1 only in the β-anomers while C-5 couples to C-1 only in the α-anomers. C-6 and C-2 always couple to C-1 in both anomeric species. The alkaline degradation of glucose [1-13 C] to saccharinic acids was followed by 13C-NMR. The conversion of glucose [1-13 C] to fructose-1,6-bisphosphate [1,6-13 C] by enzymes of the glycolytic pathway was shown as an example of the use of 13C-enriched carbohydrates to elucidate biochemical pathways. In a large number of glycosyl phosphates the 31P to H-1 and 31P to C-2 coupling constants demonstrate that in the preferred conformation the phosphate group lies between the O-5 and the H-1 of the pyranose ring. The influence of paramagnetic Mn2+ ions on the proton decoupled 13C-NMR spectra of uridine diphosphate N-acetylglucosamine indicates that the Mn2+ interacts strongly with the pyrophosphate moiety and with the carbonyl groups of the uracil and N-acetyl groups.Keywords
This publication has 23 references indexed in Scilit:
- Studies of proteins in solution by natural-abundance carbon-13 nuclear magnetic resonance. Spectral resolution and relaxation behavior at high magnetic field strengthsJournal of the American Chemical Society, 1977
- Nuclear magnetic resonance studies of the solution conformation of nucleoside diphosphohexoses and their componentsBiochemistry, 1976
- Magnetic resonance studies of the proximity and spatial arrangement of propionyl coenzyme A and pyruvate on a biotin-metalloenzyme, transcarboxylaseBiochemistry, 1976
- Conformational and substituent dependencies of carbon-13-carbon-13 coupling constantsJournal of the American Chemical Society, 1975
- Carbon-13 Nuclear Magnetic Resonance SpectroscopyScience, 1973
- Interaction of pyruvate with pyruvate carboxylase and pyruvate kinase as studied by paramagnetic effects on carbon-13 relaxation ratesBiochemistry, 1973
- Carbon‐13 nuclear magnetic resonance spectroscopy of living cells and their metabolism of a specifically labeled 13C substrateFEBS Letters, 1972
- Orientational Dependance of Vicinal and Geminal 13C–1H CouplingCanadian Journal of Chemistry, 1972
- Configurational and conformational influences on the carbon-13 chemical shifts of some carbohydratesCanadian Journal of Chemistry, 1970
- Nuclear magnetic resonance spectroscopy. Carbon-13 spectra of some pentose and hexose aldopyranosesJournal of the American Chemical Society, 1970