The mechanism for cleavage of three typical glucosidic bonds induced by hydroxyl free radical
| Autor: | Yingai Piao, Yujie Dai, Shiru Jia, Xiuli Zhang, Chunfu Shao, Min Wang, Tongcun Zhang, Man Shuli, Kui Lu, Huiqian Hu |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Sucrose
Polymers and Plastics Hydrogen Radical Oligosaccharides chemistry.chemical_element Fructose 02 engineering and technology 010402 general chemistry Hydrogen atom abstraction Ring (chemistry) 01 natural sciences chemistry.chemical_compound Polymer chemistry Materials Chemistry Monosaccharide Molecule Organic chemistry Maltose chemistry.chemical_classification Hydroxyl Radical Organic Chemistry Water 021001 nanoscience & nanotechnology 0104 chemical sciences Solvent Glucose chemistry Hydroxyl radical 0210 nano-technology Oxidation-Reduction |
| Zdroj: | Carbohydrate Polymers. 178:34-40 |
| ISSN: | 0144-8617 |
| Popis: | A novel mechanism for cleavage of three typical α(1→2), α(1→4) and β(1→4) glucosidic bonds induced by hydroxyl free radical was examined with DFT theory at B3LYP/6-31+G(d,p) level using PCM water solvent model. It was found that the hydrogen abstraction from the CH bonds outside the saccharide rings could induce the hydrogen transfer from the hydroxyl at the radical carbon to the oxygen atom of saccharide ring with the mediation of water, which led to the opening of saccharide ring and the breakage of glucosidic bonds. Alternatively, the hydrogen in COH outside the saccharide ring of maltose and sucrose could also transfer to the adjacent glucosidic oxygen atom with a water molecule mediation to make glucosidic bond break directly. Based on this study, it can be well explained the experimental results that the oxidation of some oligosaccharides with hydroxyl free radicals can produce molecules of glucose, fructose and other monosaccharides. |
| Databáze: | OpenAIRE |
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