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Título: | Exploration of the use of an acylsulfonamide safety-catch linker for the polymer-supported synthesis of hyaluronic acid oligosaccharides |
Autor: | Paz, José L. de CSIC ORCID; Kayser, M. Mar CSIC; Macchione, Giuseppe CSIC; Nieto, Pedro M. CSIC ORCID | Palabras clave: | Hyaluronic acid Glycosylation Oligosaccharide synthesis Polymer-supported synthesis Sulfonamide Polyethylene glycol |
Fecha de publicación: | 30-mar-2010 | Editor: | Elsevier | Citación: | Carbohydrate Research 345(5): 565-571 (2010) | Resumen: | The synthesis of hyaluronic acid oligosaccharides on polyethylene glycol (PEG) using an acylsulfonamide linker has been explored. Hyaluronic acid is a challenging synthetic target that usually involves the condensation of highly disarmed glucuronic acid building blocks. Amine-ended PEG monomethyl ether was efficiently functionalized with a hydroxyl-terminated acylsulfonamide linker. Suitably protected d-glucosamine (GlcN) and d-glucuronic acid (GlcA) monosaccharide building blocks were coupled to the polymer acceptor using the trichloroacetimidate glycosylation method. The sulfonamide safety-catch linker enables simultaneous cleavage of the monosaccharide from the polymer and orthogonal functionalization for further (bio)-conjugation of the sugar sample. Subsequent glycosylation of PEG-bound glycosyl acceptor to generate hyaluronic acid oligosaccharide chain failed. Model glycosylation experiments in solution and on soluble support using the same unreactive acceptors and donors allows for the synthesis of an orthogonally protected hyaluronic acid disaccharide and suggest that the encountered difficulties could be attributed to the presence of the N-acylsulfonamide. | Descripción: | 23 páginas, 5 esquemas | Versión del editor: | http://dx.doi.org/10.1016/j.carres.2009.12.021 | URI: | http://hdl.handle.net/10261/36187 | DOI: | 10.1016/j.carres.2009.12.021 | ISSN: | 0008-6215 |
Aparece en las colecciones: | (IIQ) Artículos |
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Carbohydrate res 2010.doc | 231 kB | Microsoft Word | Visualizar/Abrir |
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