title: Synthesis of hyaluronic acid oligomers using chemoselective and one-pot strategies.
abstract: An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.
authors.affiliation: Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Jasper
authors.initials: J
authors.lastname: Dinkelaar
authors.forename: Henrik
authors.initials: H
authors.lastname: Gold
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Jeroen D C
authors.initials: JD
authors.lastname: Codée
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
mesh_terms: D005944:Glucosamine / Q000737:chemistry; D006820:Hyaluronic Acid / Q000138:chemical synthesis*; D011108:Polymers / Q000138:chemical synthesis*; D013865:Thioglycosides / Q000737:chemistry
chemical_list: D011108:Polymers; D013865:Thioglycosides; D006820:Hyaluronic Acid; D005944:Glucosamine