title: A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides.
abstract: d-Glucosamine derivatives bearing latent O4 functionality provide modified H/HS-type disaccharide donors for a final stage capping approach enabling introduction of conjugation-suitable, non-reducing terminal functionality to biologically important glycosaminoglycan oligosaccharides. Application to the synthesis of the first O4-terminus modified synthetic LMWH decasaccharide and an HS-like dodecasaccharide is reported.
authors.affiliation: Manchester Institute of Biotechnology and School of Chemistry, 131 Princess Street, University of Manchester M1 7DN, UK. gardiner@manchester.ac.uk.
authors.forename: Gavin J
authors.initials: GJ
authors.lastname: Miller
authors.forename: Karl R
authors.initials: KR
authors.lastname: Broberg
authors.forename: Claire
authors.initials: C
authors.lastname: Rudd
authors.forename: Madeleine R
authors.initials: MR
authors.lastname: Helliwell
authors.forename: Gordon C
authors.initials: GC
authors.lastname: Jayson
authors.forename: John M
authors.initials: JM
authors.lastname: Gardiner
mesh_terms: D000478:Alkylation; D000925:Anticoagulants / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006025:Glycosaminoglycans / Q000138:chemical synthesis / Q000737:chemistry*; D006493:Heparin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006495:Heparin, Low-Molecular-Weight / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008958:Models, Molecular; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000925:Anticoagulants; D004187:Disaccharides; D006025:Glycosaminoglycans; D006495:Heparin, Low-Molecular-Weight; D009844:Oligosaccharides; D006493:Heparin; D005944:Glucosamine