6533b7defe1ef96bd1275de6
RESEARCH PRODUCT
Reaction pathways of glucose oxidation by ozone under acidic conditions.
Roger GuilardOlivier MarcqAlain TrichetJean-michel Barbesubject
ArabinoseOzoneDecarboxylationInorganic chemistry02 engineering and technologyUronic acidoxidation -mechanism01 natural sciencesBiochemistryGluconatesMass SpectrometryAnalytical Chemistrychemistry.chemical_compoundOzoneD-Glucose[ CHIM.OTHE ] Chemical Sciences/OtherOrganic chemistrydecarboxylationComputingMilieux_MISCELLANEOUS010405 organic chemistryOrganic ChemistryGeneral MedicineCarbon-13 NMRCarbon DioxideHydrogen-Ion Concentration021001 nanoscience & nanotechnologyArabinoseketo acidCarbon0104 chemical sciencesuronic acidGlucosechemistryCarbon dioxideGluconic acid0210 nano-technology[CHIM.OTHE]Chemical Sciences/OtherOxidation-Reductionpectic aciddescription
The ozonation of d-glucose-1-(13)C, 2-(13)C, and 6-(13)C was carried out at pH 2.5 in a semi-batch reactor at room temperature. The products present in the liquid phase were analyzed by GC-MS, HPAEC-PAD, and (13)C NMR spectroscopy. Common oxidation products of glucose have also been submitted to identical ozonation conditions. For the first time, a pentaric acid was identified and its formation quantitatively correlated to the loss of C-6 of glucose in the form of carbon dioxide. Potential mechanisms for the formation of this pentaric acid are discussed. The well-accepted pathway involving the anomeric position in glucose, gluconic acid, arabinose, and carbon dioxide is reinvestigated. The origin of small molecules such as tartaric, erythronic, and oxalic acids is clarified. Finally, new reaction pathways and tentative mechanisms consistent with the formation of ketoaldonic acids and smaller acids are proposed.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2009-05-18 | Carbohydrate research |