Determination of proton-proton distances in 2-acetamido-2-deoxy monosaccharides from 1H NMR relaxation measurements in solution

László Szilágyi, Péter Forgó

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Abstract

Determination of selective and biselective 1H spin-lattice relaxation rates combined with steady-state and transient 1H1H NOE data allowed calculation of intramolecular proton-proton distances in 2-acetamido-2-deoxy-d-glucosides (1a an 1b), 2-acetamido-2-deoxy-d-mannoses (5a and 5b) and their acetylated derivatives. These measurements were supplemented by DESERT studies using derivatives selectively labeled by 2H at position 2. These distance data are in good correlation with literature values obtained by X-ray crystallography. Interproton distance measurements allow the determination of relative configurations, including that of the anomeric carbon, in hexopyranose rings in cases where other methods, like those based on scalar coupling constants, fail.

Original languageEnglish
Pages (from-to)129-144
Number of pages16
JournalCarbohydrate Research
Volume247
Issue numberC
DOIs
Publication statusPublished - Sep 2 1993

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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