13C Nuclear Magnetic Relaxation of Carbohydrate Molecules in Solution

  • Photis Dais
Conference paper
Part of the NATO ASI Series book series (volume 87)


Nuclear magnetic resonance spectroscopy is a very powerful tool for analyzing the conformation and molecular architecture of carbohydrate molecules. Both ID and 2D methodologies have provided valuable information about small and large molecules, ranging from the anomeric configuration of a monosaccharide to the more complex problem of the sequence of monosaccharide residues that constitute an oligo-, or polysaccharides.


Spectral Density Function Hydroxymethyl Group Neuraminic Acid Nuclear Magnetic Relaxation Nuclear Overhauser Enhancement 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Allerhand A, Doddrell D and Komorowski D (1971) Natural abundance carbon-13 partially relaxaed Fourier transform nuclear magnetic resonance spectra of complex molecules. J. Chem. Phys. 55: 189–198CrossRefGoogle Scholar
  2. Allerhand A and Doddrell D (1971) Strategies in the application of partially relaxed Fourier transform nuclear magnetic resonance spectroscopy in assignments of carbon-13 resonances of complex molecules. Stachyose. J. Am. Chem. Soc. 93: 2777–2779CrossRefGoogle Scholar
  3. Berry JM, Hall LD and Wong KF (1977) Concerning the tumbling motion of disaccharides in aqueous solution. Carbohydr. Res. 56: C16-C20CrossRefGoogle Scholar
  4. Bock K and Lemieux RU (1982) The conformational properties of sucrose in aqueous solution: Intramolecular hydrogen bonding. Carbohydr. Res. 100: 63–74CrossRefGoogle Scholar
  5. Czarniecki MF and Thornton ER (1976) 13C spin-lattice relaxation in neuraminic acids. Evidence for an unsual itramolecular hydrogen bonding network. J. Am. Chem. Soc. 98: 1023–1025CrossRefGoogle Scholar
  6. Czarniecki MF and Thornton ER (1977) Carbon-13 nuclear magnetic spin-lattice relaxation in the N-acetylneuraminic acids. Probes for internal dynamics and conformational analysis. J. Am. Chem. Soc. 99: 8273–8278CrossRefGoogle Scholar
  7. Czarniecki MF and Thornton ER (1977) Carbon-13 nuclear magnetic resonance of ganglioside sugars. Spin-lattice relaxation probes for structure and microdynamics of cell surface carbohydrates. J. Am. Chem. Soc. 99: 8279–8282CrossRefGoogle Scholar
  8. Dais P, Shing TK and Perlin AS (1983) Proton spin-lattice relaxation rates and nuclear Overhauser enhancement, in relation to the stereochemistry of p-D-mannopyranose 1,2-orthoacetates. Carbohydr. Res. 122: 305–313CrossRefGoogle Scholar
  9. Dais P and Perlin AS (1983) Motional behavior of 2,3: 5,6-di-O-isopropylidene-a-D-mannopyranoside in solution. A 13C spin-lattice relaxation study. Can. J. Chem. 61: 1542- 1548CrossRefGoogle Scholar
  10. Dais P and Perlin AS (1985) Stabilization of the p-furanose form, and kinetics of the tautomerization on D-fructose in dimethylsulfoxide. Carbohydr. Res. 136: 215–223CrossRefGoogle Scholar
  11. Dais P and Fainos G (1986) Motional behavior of “asperlin” in solution. A 13C spin-lattice relaxation study. Can. J. Chem. 69: 560–565CrossRefGoogle Scholar
  12. Dais P and Perlin AS (1986) Chemical shifts of the methyl groups in di-O-isopropylidene furanoses, and their relationship to molecular conformation and site of ring fusion. Spinlattice relaxation measurements and motional characteristics. Carbohydr. Res. 146177–191CrossRefGoogle Scholar
  13. Dais P and Perlin AS (1987) Intramolecular hydrogen-bonding and solvation contributions to the relative stability of the p-furanose form of D-fructose in dimethylsulfoxide. Carbohydr. Res. 169: 159–169CrossRefGoogle Scholar
  14. Dais P and Perlin AS (1989) A 13C spin-lattice relaxation study of solvent effects on the rotational dynamic of methyl glucosides. Carbohydr. Res. 194 288–195CrossRefGoogle Scholar
  15. Harvey JM and Symons MCR (1978) The hydration of monosaccharides. An NMR study. J. Solution Chem. 7: 571–586CrossRefGoogle Scholar
  16. Jaques LW, Giant S and Weltner Jr. W (1980) Spin-lattice relaxation times for two isomers of N-acetylneuraminyl lactose. Carbohydr. Res. 80: 207–211CrossRefGoogle Scholar
  17. Kovacs H, Bangley S and Kowalewski J (1989) Motional properties of two disaccharides in solution as studied by carbon-13 relaxation and NOE outside the extreme narrowing region. J. Magn. Res. 85: 530–541CrossRefGoogle Scholar
  18. London RE (1978) On the interpretation of 13C spin-lattice relaxation sesulting from ring puckering in proline. J. Am. Chem. Soc. 100: 2678–2685CrossRefGoogle Scholar
  19. Lyerla Jr. JR and Levy GC (1974) Carbon-13 nuclear spin relaxation. In: Topics in carbon- 13 NMR spectroscopy. Wiley & Sons New York. Vol. 1: 79–148Google Scholar
  20. McCain DC and Markley JL (1986) The solution conformation of sucrose: Concentration and temperature dependence. Carbohydrate Res. 152: 73–80CrossRefGoogle Scholar
  21. McCain DC and Marklay JL (1986) Rotational spectral density functions for aqueous fructose: Experimental determination using 13C NMR. J. Am. Chem. Soc. 108: 4259–4264CrossRefGoogle Scholar
  22. Neszmelyi A, Liptak A and Nanasi P (1977) 13C NMR relaxation times and chemical shifts of the exo and en do isomers of dioxolane-type benzylidene acetals of carbohydrates: Determination of the absolute configuration. Carbohydr. Res. 58: C7-C9CrossRefGoogle Scholar
  23. Neszmelyi A, Tori K and Lukacs G (1977) Use of the carbon-13 spin-lattice relaxation times for sugar sequence determination in steroidal oligosaccharides. Chem. Commun. 613–614Google Scholar
  24. Serianni AS and Barker R (1982) 13C spin-lattice relaxation times of [1-13C]- enriched carbohydrates. J. Magn. Reson. 49: 335–340CrossRefGoogle Scholar
  25. Serianni AS and Barker R (1984) [13C]- enriched tetroses and tetrofuranosides: an evaluation of the relationship between NMR parameters and furanosyl ring conformation. J. Org. Chem. 49: 3292–3300CrossRefGoogle Scholar
  26. Woessner DE (1962) Nuclear spin-relaxation in ellipsoids undergoing rotational Brownian motion. J. Chem. Phys. 37: 647–654CrossRefGoogle Scholar
  27. Wu GD, Serianni AS and Barker (1983) Stereoselective exchange of methylene protons in methyl tetrofuranosides: Hydroxymethyl group conformations in methyl pentofuranosides. J. Org. Chem. 48: 1750–1757CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1994

Authors and Affiliations

  • Photis Dais
    • 1
  1. 1.Department of ChemistryUniversity of CreteIraklion, CreteGreece

Personalised recommendations