Simultaneous formation of 3-deoxy-d-threo-hexo-2-ulose and 3-deoxy-d-erythro-hexo-2-ulose during the degradation of d-glucose derived Amadori rearrangement products: Mechanistic considerations
| Autor: | Clemens Mügge, Sophie Krüger, Martin Kaufmann, Lothar W. Kroh |
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| Rok vydání: | 2017 |
| Předmět: |
Magnetic Resonance Spectroscopy
Stereochemistry Substituent Protonation 010402 general chemistry 01 natural sciences Biochemistry Analytical Chemistry chemistry.chemical_compound Deprotonation D-Glucose Amadori rearrangement Ketoses Amino Acids chemistry.chemical_classification 010405 organic chemistry Hydrogen bond Organic Chemistry Galactose General Medicine Nuclear magnetic resonance spectroscopy 0104 chemical sciences Amino acid Maillard Reaction Glucose chemistry |
| Zdroj: | Carbohydrate research. |
| ISSN: | 1873-426X |
| Popis: | Analyzing classical model reaction systems of Amadori rearrangement products (ARP) it became apparent that the formation of 3-deoxy- d -threo-hexo-2-ulose (3-deoxygalactosone, 3-DGal) during the degradation of ARPs is highly dependent on pH and the amino acid residue of the respective ARP. Based on a detailed analysis of the NMR chemical shifts of the sugar moieties of different ARPs, it could be derived that the formation of 3-DGal is sensitive to the stability of a co-operative hydrogen bond network which involves HO-C3, the deprotonated carboxyl functionality and the protonated amino nitrogen of the amino acid substituent. Participating in this bond network, HO-C3 is partially protonated which facilitates the elimination of water at C3. Based on that, a new mechanism of 3-deoxyglycosone formation is proposed. |
| Databáze: | OpenAIRE |
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