Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

One-bond carbon-proton coupling constants: Angular dependence in β-linked oligosaccharides

  • 91 Accesses

  • 34 Citations


The angular dependence of1JC,H in model compounds related to β-linked oligosaccharides has been established by FPT INDO quantum chemical calculations. Values calculated for models of (1 → 1)-, (1 → 2)-, (1 → 3)- and (1 → 4)-linked disaccharides were compared, and the effect of the orientation of HO-2 elucidated. The angular dependence of1JC,H on the torsional angles ΦH and ΨH and the solvent dielectric constant (s) was characterized in the form:1JC,H = A cos2ϖ+B cosϖ + C sin2ϖ + D since + E + Fe. The1JC,H values, measured by DEPT methods for C-1-H-1 and C-X′-H-X′ in cellobiose, cyclic trisaccharide and hexopyranoses were used to adjust the calculated angular dependences. Based on the occurrence of the conformers for agarobiose, neoagarobiose, mannobiose and methyl β-xylobioside, the thermodynamically averaged <1JC,H > values were calculated. The results obtained (<1JC-1,H-1 > 162.4, <1JC-4′, H-4′ > 147.6 Hz for methyl β-xylobioside; <1JC-1,H-1 > 162.4 and <1JC-4′,H-4′] > 147.6 Hz for mannobiose; <1JC-1,H-1 > 162.8 Hz for neo agarobiose and <1JC-1,H-1 > 163.2 Hz for agarobiose) agree well with the experimental values of 162.7, 147.5, 160.4, 147.2, 160.9 and 165.7 Hz, respectively.

This is a preview of subscription content, log in to check access.


  1. Bonas, G., Vignon, M.R. and Pérez, S. (1991)Carbohydr. Res.,211, 191–205.

  2. Box, M.J. (1965)Comput. J.,8, 45–52.

  3. Davies, D.B., MacCoss, M. and Danyluk, S.S. (1984)J. Chem. Soc., Chem. Commun., 536–538.

  4. Davies, D.B., Rajani, P. and Sadikot, H. (1985)J. Chem. Soc. Perkin Trans. 11, 279–285.

  5. Hricovini, M. and Tvaroska, I. (1990)Magn. Res. Chem.,28, 862–866.

  6. Hricovini, M., Tvaroska, I. and Hirsch, J. (1990)Carbohydr. Res.,198, 193–203.

  7. Jimenez-Barbero, J., Bouffar-Roupe, C., Rochas, C. and Pérez, S. (1989)Int. J. Biol. Macromol.,11, 265–272.

  8. Pople, J.A., McIver Jr., J.W. and Ostlund, N.Y. (1968)J. Chem. Phys.,49, 2960–2965.

  9. Tvaroska, I. (1984)Biopolymers,23, 1951–1960.

  10. Tvaroska, I., Pérez, S., Noble, O. and Taravel, F. (1987)Biopolymers,26, 1499–1508.

  11. Tvaroska, I. and Bleha, T. (1989)Adv. Carbohydr. Chem. Biochem.,47, 45–123.

  12. Tvaroska, I. (1990)Carbohydr. Res.,206, 55–64.

  13. Tvaroska, I. and Taravel, F.R. (1991)Carbohydr. Res.,221, 83–94.

Download references

Author information

Correspondence to François R. Taravel.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Tvaroska, I., Taravel, F.R. One-bond carbon-proton coupling constants: Angular dependence in β-linked oligosaccharides. J Biomol NMR 2, 421–430 (1992). https://doi.org/10.1007/BF02192806

Download citation


  • One-bond carbon-proton coupling constants
  • β-Linked oligosaccharides
  • Angular dependence