完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.author | Yeh, Che-Jui | en_US |
dc.contributor.author | Zulueta, Medel Manuel L. | en_US |
dc.contributor.author | Li, Yaw-Kuen | en_US |
dc.contributor.author | Hung, Shang-Cheng | en_US |
dc.date.accessioned | 2020-10-05T02:01:07Z | - |
dc.date.available | 2020-10-05T02:01:07Z | - |
dc.date.issued | 2020-07-28 | en_US |
dc.identifier.issn | 1477-0520 | en_US |
dc.identifier.uri | http://dx.doi.org/10.1039/d0ob01048k | en_US |
dc.identifier.uri | http://hdl.handle.net/11536/155151 | - |
dc.description.abstract | Hyaluronic acid (HA) is a ubiquitous glycosaminoglycan in the extracellular matrix and a ligand of CD44, a transmembrane glycoprotein that is important in cell migration. Crystal and NMR studies found a hexasaccharide of the pattern (GlcA-GlcNAc)(3)as the shortest HA that could bind to CD44, but molecular dynamics simulations indicated that a tetrasaccharide of the pattern (GlcNAc-GlcA)(2)is the key structure interacting with CD44. Access to oligomers with such a repeat pattern is crucial in binding studies with CD44. Here we developed a synthetic procedure to afford the HA oligosaccharides with the GlcNAc-GlcA repeating unit and measured the binding interaction between these sugars and human CD44 by isothermal titration calorimetry (ITC). During the chemical synthesis, we successfully generated the beta-glycosidic bond in the absence of neighbouring group participation and overcome the issues in the oxidation step. In addition, ammonia-free dissolving metal reduction for debenzylation and azido reduction has been applied in carbohydrate synthesis for the first time. ITC analysis revealed that the HA tetrasaccharide (GlcNAc-GlcA)(2)could indeed interact and bind to the human CD44. | en_US |
dc.language.iso | en_US | en_US |
dc.title | Synthesis of hyaluronic acid oligosaccharides with a GlcNAc-GlcA repeating pattern and their binding affinity with CD44 | en_US |
dc.type | Article | en_US |
dc.identifier.doi | 10.1039/d0ob01048k | en_US |
dc.identifier.journal | ORGANIC & BIOMOLECULAR CHEMISTRY | en_US |
dc.citation.volume | 18 | en_US |
dc.citation.issue | 28 | en_US |
dc.citation.spage | 5370 | en_US |
dc.citation.epage | 5387 | en_US |
dc.contributor.department | 應用化學系 | zh_TW |
dc.contributor.department | Department of Applied Chemistry | en_US |
dc.identifier.wosnumber | WOS:000550965600009 | en_US |
dc.citation.woscount | 0 | en_US |
顯示於類別: | 期刊論文 |