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Accurate Quantitative Isotopic 13C NMR Spectroscopy for the Determination of the Intramolecular Distribution of 13C in Glucose at Natural Abundance.

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Title: Accurate Quantitative Isotopic 13C NMR Spectroscopy for the Determination of the Intramolecular Distribution of 13C in Glucose at Natural Abundance.
Authors: Gilbert, Alexis1, Silvestre, Virginie1, Robins, Richard J.1, Remaud, Gerald S.1 gerald.remaud@univ-nantes.fr
Source: Analytical Chemistry. 11/1/2009, Vol. 81 Issue 21, p8978-8985. 8p.
Subjects: Glucose, Nuclear magnetic resonance spectroscopy, Isotopes, Metabolites, Carbon, Fructose, Biosynthesis
Abstract: In order to understand 13C isotope distributions in glucose and its metabolites, it is necessary to measure the internal 13C distribution at natural abundance. These data, however, are not directly accessible, even by quantitative isotopic 13C NMR spectrometry, due to anomerization at the C-1 position. A strategy has been developed that overcomes this difficulty by converting glucose via a three-step synthesis into 3,5,6-triacetyl-1,2-O-isopropylidene-α-D-glucofuranose (TAMAGF). This compound provides a satisfactory molecular probe to measure the site-specific 13C/12C ratios in glucose by 13C NMR. It is shown that the isotopic 13C NMR signal gives sufficient precision (repeatability standard deviation ⩽0.8%o) for routine use for the determination of the 13C abundance of each carbon atom position in glucose. Thus, it can be seen that the internal 13C distribution of glucose biosynthesized by the C3 and C4 metabolic pathways differs markedly. Furthermore, the method is suitable for determining the isotope ratio in the glucose moiety of sucrose and, possibly, in free fructose and the fructose moiety of sucrose. [ABSTRACT FROM AUTHOR]
Copyright of Analytical Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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  Data: Accurate Quantitative Isotopic <superscript>13</superscript>C NMR Spectroscopy for the Determination of the Intramolecular Distribution of 13C in Glucose at Natural Abundance.
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  Data: <searchLink fieldCode="JN" term="%22Analytical+Chemistry%22">Analytical Chemistry</searchLink>. 11/1/2009, Vol. 81 Issue 21, p8978-8985. 8p.
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  Data: <searchLink fieldCode="DE" term="%22Glucose%22">Glucose</searchLink><br /><searchLink fieldCode="DE" term="%22Nuclear+magnetic+resonance+spectroscopy%22">Nuclear magnetic resonance spectroscopy</searchLink><br /><searchLink fieldCode="DE" term="%22Isotopes%22">Isotopes</searchLink><br /><searchLink fieldCode="DE" term="%22Metabolites%22">Metabolites</searchLink><br /><searchLink fieldCode="DE" term="%22Carbon%22">Carbon</searchLink><br /><searchLink fieldCode="DE" term="%22Fructose%22">Fructose</searchLink><br /><searchLink fieldCode="DE" term="%22Biosynthesis%22">Biosynthesis</searchLink>
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  Data: In order to understand 13C isotope distributions in glucose and its metabolites, it is necessary to measure the internal 13C distribution at natural abundance. These data, however, are not directly accessible, even by quantitative isotopic 13C NMR spectrometry, due to anomerization at the C-1 position. A strategy has been developed that overcomes this difficulty by converting glucose via a three-step synthesis into 3,5,6-triacetyl-1,2-O-isopropylidene-α-D-glucofuranose (TAMAGF). This compound provides a satisfactory molecular probe to measure the site-specific 13C/12C ratios in glucose by 13C NMR. It is shown that the isotopic 13C NMR signal gives sufficient precision (repeatability standard deviation ⩽0.8%o) for routine use for the determination of the 13C abundance of each carbon atom position in glucose. Thus, it can be seen that the internal 13C distribution of glucose biosynthesized by the C3 and C4 metabolic pathways differs markedly. Furthermore, the method is suitable for determining the isotope ratio in the glucose moiety of sucrose and, possibly, in free fructose and the fructose moiety of sucrose. [ABSTRACT FROM AUTHOR]
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  Data: <i>Copyright of Analytical Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1021/ac901441g
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      – Code: eng
        Text: English
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        StartPage: 8978
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      – SubjectFull: Glucose
        Type: general
      – SubjectFull: Nuclear magnetic resonance spectroscopy
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      – SubjectFull: Isotopes
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      – SubjectFull: Metabolites
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      – SubjectFull: Carbon
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      – SubjectFull: Fructose
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      – SubjectFull: Biosynthesis
        Type: general
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      – TitleFull: Accurate Quantitative Isotopic 13C NMR Spectroscopy for the Determination of the Intramolecular Distribution of 13C in Glucose at Natural Abundance.
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            NameFull: Gilbert, Alexis
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            NameFull: Silvestre, Virginie
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              M: 11
              Text: 11/1/2009
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