title: A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy.
abstract: A novel flexible assembly strategy is described for the modular synthesis of heparin and heparan sulfates. The reported strategy uses monomeric building blocks to construct the oligosaccharide chain to attain a maximum degree of flexibility. In the assembly, 1-hydroxyl glucosazido- and 1-thio uronic acid donors are combined in a sequential glycosylation protocol using sulfonium triflate activator systems. The key 1-thio uronic acids were obtained in an efficient manner from diacetone glucose employing a chemo- and regioselective oxidation of partially protected glucose and idose thioglycosides.
authors.affiliation: Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, PO Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Jeroen D C
authors.initials: JD
authors.lastname: Codée
authors.forename: Bas
authors.initials: B
authors.lastname: Stubba
authors.forename: Marialuisa
authors.initials: M
authors.lastname: Schiattarella
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Constant A A
authors.initials: CA
authors.lastname: van Boeckel
authors.forename: Jacques H
authors.initials: JH
authors.lastname: van Boom
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
mesh_terms: D002240:Carbohydrate Sequence; D006031:Glycosylation; D006493:Heparin / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D014574:Uronic Acids / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D009844:Oligosaccharides; D014574:Uronic Acids; D006493:Heparin