Synthesis and conformational analysis of d-gluco-pyranosyl-(6,6')-d-gluco-pyranuronate, a model compound for the inter-glycan 6,6'-ester linkage
| Autor: | Andreas H. Franz, Sven Hackbusch, Amelia Watson |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Glycan
Magnetic Resonance Spectroscopy Stereochemistry Disaccharide Molecular Conformation Molecular Dynamics Simulation 010402 general chemistry Disaccharides 01 natural sciences Biochemistry Analytical Chemistry Molecular dynamics chemistry.chemical_compound Polysaccharides Carbohydrate Conformation Molecule Linkage (software) biology 010405 organic chemistry Organic Chemistry General Medicine Nuclear magnetic resonance spectroscopy Solution phase 0104 chemical sciences chemistry biology.protein Carbohydrate conformation |
| Zdroj: | Carbohydrate research. |
| ISSN: | 1873-426X |
| Popis: | The synthesis of a 6,6'-ester linked disaccharide analog model compound was achieved in five steps from d-glucose and featured a key oxidative esterification transformation. The synthesized d-gluco-pyranosyl-(6,6')-d-gluco-pyranuronate was characterized in D2O using NMR spectroscopy. Using the experimental data together with molecular dynamics simulations (TIP3P, water), a model of the compound's conformational behavior was established. The effect of the 6,6'-ester linkage on the solution phase structure was compared to that of the previously reported 6,6'-ether linkage in a disaccharide analog. Based on the established models, the ester linkage was found to have a profound effect on the overall shape of the molecule. |
| Databáze: | OpenAIRE |
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