A1H-NMR and MD study of intramolecular hydrogen bonds in methyl β-cellobioside

B.R. Leeflang, J.F.G. Vliegenthart, L.M.J. Kroon-Batenburg, B.P. Van Eijck, J. Kroon

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

The existence of an HO-3...O-5' intramolecular hydrogen bond in methyl β-cellobioside in solution in Me2SO-d6and H2O-CD3OD (4:1 w/w) was studied by 500-MHz1H-NMR spectroscopy and MD simulations. Temperature coefficients for the chemical shift of the hydroxyl resonances in these solvents were determined and the rates of proton exchange in the latter solvent were obtained from NOE data. With H2O-CD3OD as the solvent, the HO-3...O-5' hydrogen bond was insignificant, but its presence in Me2SO-d6was confirmed.
Original languageEnglish
Pages (from-to)41-61
Number of pages21
JournalCarbohydrate Research
Volume230
Issue number1
DOIs
Publication statusPublished - 1 Jun 1992

Keywords

  • cellobioside
  • glycoside
  • unclassified drug
  • article
  • chemical structure
  • mathematics
  • nuclear magnetic resonance
  • theory

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