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 Carrera, Jose Luis de, Nieto Mesa, Pedro Manuel
Tipo de recurso: artículo
Estado:Versión enviada para evaluación y publicación
Fecha de publicación:2014
País:España
Institución:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/69625
Acceso en línea:https://hdl.handle.net/11441/69625
https://doi.org/10.1016/j.carres.2014.05.007
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.