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

doi:10.1007/s10858-018-0209-y

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^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	93-103
Number of pages	11
Journal	Journal of Biomolecular NMR
Volume	72
Issue number	1-2
DOIs	https://doi.org/10.1007/s10858-018-0209-y
State	Published - 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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10.1007/s10858-018-0209-y

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title = "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",

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.",

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

author = "Michal Rivlin and Gil Navon",

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year = "2018",

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doi = "10.1007/s10858-018-0209-y",

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AU - Navon, Gil

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N2 - 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.

AB - 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.

KW - 3-O-Methyl-d-glucose (3OMG)

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KW - Chemical exchange saturation transfer (CEST)

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KW - Spin lock (SL)

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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

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Keywords

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