3-O-Methyl-d-glucose mutarotation and proton exchange rates assessed by 13C, 1H NMR and by chemical exchange saturation transfer and spin lock measurements

Michal Rivlin, Gil Navon

Research output: Contribution to journalArticlepeer-review

Abstract

3-O-Methyl-d-glucose (3OMG) was recently suggested as an agent to image tumors using chemical exchange saturation transfer (CEST) MRI. To characterize the properties of 3OMG in solution, the anomeric equilibrium and the mutarotation rates of 3OMG were studied by 1H and 13C NMR. This information is essential in designing the in vivo CEST experiments. At room temperature, the ratio of α and β 3OMG anomers at equilibrium was 1:1.4, and the time to reach 95% equilibrium was 6 h. The chemical exchange rates between the hydroxyl protons of 3OMG and water, measured by CEST and spin lock at pH 6.14 and a temperature of 4 °C, were in the range of 360–670 s−1.

Original languageEnglish
Pages (from-to)93-103
Number of pages11
JournalJournal of Biomolecular NMR
Volume72
Issue number1-2
DOIs
StatePublished - 1 Oct 2018

Keywords

  • 3-O-Methyl-d-glucose (3OMG)
  • Anomeric equilibrium
  • Chemical exchange saturation transfer (CEST)
  • Mutarotation kinetics
  • NMR spectroscopy
  • Spin lock (SL)

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