title: Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach.
abstract: 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.
authors.affiliation: Glycosystems Laboratory, Instituto de Investigaciones Químicas (IIQ), Centro de Investigaciones Científicas Isla de La Cartuja, CSIC and Universidad de Sevilla, Americo Vespucio, 49, 41092 Sevilla, Spain.
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Macchione
authors.affiliation: Glycosystems Laboratory, Instituto de Investigaciones Químicas (IIQ), Centro de Investigaciones Científicas Isla de La Cartuja, CSIC and Universidad de Sevilla, Americo Vespucio, 49, 41092 Sevilla, Spain. Electronic address: jlpaz@iiq.csic.es.
authors.forename: José L
authors.initials: JL
authors.lastname: de Paz
authors.affiliation: Glycosystems Laboratory, Instituto de Investigaciones Químicas (IIQ), Centro de Investigaciones Científicas Isla de La Cartuja, CSIC and Universidad de Sevilla, Americo Vespucio, 49, 41092 Sevilla, Spain.
authors.forename: Pedro M
authors.initials: PM
authors.lastname: Nieto
mesh_terms: D002240:Carbohydrate Sequence; D060326:Chemistry Techniques, Synthetic; D006031:Glycosylation; D006820:Hyaluronic Acid / Q000737:chemistry*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D014312:Trisaccharides / Q000138:chemical synthesis
chemical_list: D009844:Oligosaccharides; D014312:Trisaccharides; D006820:Hyaluronic Acid
keywords: Carbohydrates; Fluorous tag; Glucuronic acid; Glycosylation; Hyaluronic acid; Oligosaccharide synthesis