TEMPO-mediated oxidation of maltodextrins and d-glucose: effect of pH on the selectivity and sequestering ability of the resulting polycarboxylates
| Autor: | Jean‐Francois Thaburet, Guy Quéguiner, Mathias Ibert, Nabyl Merbouh, Francis Marsais |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
Sodium
Inorganic chemistry Oligosaccharides chemistry.chemical_element Primary alcohol Polysaccharide Biochemistry Antioxidants Gas Chromatography-Mass Spectrometry Analytical Chemistry Cyclic N-Oxides chemistry.chemical_compound Glucuronic Acid Polysaccharides D-Glucose Organic chemistry Nuclear Magnetic Resonance Biomolecular chemistry.chemical_classification Depolymerization Organic Chemistry General Medicine Hydrogen-Ion Concentration Glucose chemistry Polymerization Yield (chemistry) Calcium Spin Labels Selectivity Oxidation-Reduction |
| Zdroj: | Carbohydrate Research. 330:21-29 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/s0008-6215(00)00263-9 |
| Popis: | Maltodextrins were oxidized to polyglucuronic acids with the ternary oxidation system: NaOCl-NaBr-2,2,6,6-tetramethylpiperidine-l-oxyl (TEMPO). The chemoselective oxidation at the primary alcohol groups was shown to be strongly pH dependent. Oxidation of polysaccharides was best achieved at pH 9.5 in order to minimize depolymerization, whereas oxidation of oligosaccharides required stronger alkaline conditions (pH 11-11.5). The resulting sodium polyglucuronates present interesting sequestering properties, the best of which being obtained from maltodextrins with the highest degrees of polymerization. The same oxidation process allowed the convenient conversion of D-glucose to D-glucaric acid in high yield (> 90%), under strongly basic conditions (pH > 11.5). |
| Databáze: | OpenAIRE |
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