Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach

The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of syn...

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Detalles Bibliográficos
Autores: Macchione, Giuseppe, Paz, José L. de, Nieto, Pedro M.
Tipo de recurso: artículo
Fecha de publicación:2014
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/98747
Acceso en línea:http://hdl.handle.net/10261/98747
Access Level:acceso abierto
Palabra clave:Hyaluronic acid
Glycosylation
Fluorous tag
Oligosaccharide synthesis
Glucuronic acid
Carbohydrates
Descripción
Sumario:The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of synthetic intermediates, a fluorous-assisted strategy has been also explored. Using this approach, a hyaluronic acid trisaccharide was prepared.