title: Protecting group free synthesis of glycosyl thiols from reducing sugars in water; application to the production of N-glycan glycoconjugates.
abstract: Glycosyl thiols may be accessed from the corresponding reducing sugars in water without recourse to any sugar projecting groups by way of a DMC mediated reaction with thioacetic acid in the presence of base, and hydrolysis of the anomeric thioacetate. Glycosyl thiols produced by this method may be used to access glycoconjugates, such as glycopeptides by use of the thiol-ene click reaction.
authors.affiliation: Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand. antony.fairbanks@canterbury.ac.nz.
authors.forename: S R
authors.initials: SR
authors.lastname: Alexander
authors.affiliation: Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand. antony.fairbanks@canterbury.ac.nz.
authors.forename: D
authors.identifier: http://orcid.org/0000-0002-7149-6459
authors.initials: D
authors.lastname: Lim
authors.affiliation: School of Chemical Sciences, The University of Auckland, 23 Symonds St, Auckland 1142, New Zealand and Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, Private Bag 92019, Auckland 1142, New Zealand.
authors.forename: Z
authors.initials: Z
authors.lastname: Amso
authors.affiliation: School of Chemical Sciences, The University of Auckland, 23 Symonds St, Auckland 1142, New Zealand and Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, Private Bag 92019, Auckland 1142, New Zealand.
authors.forename: M A
authors.identifier: http://orcid.org/0000-0002-7086-4096
authors.initials: MA
authors.lastname: Brimble
authors.affiliation: Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand. antony.fairbanks@canterbury.ac.nz and Biomolecular Interaction Centre, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand.
authors.forename: A J
authors.identifier: http://orcid.org/0000-0002-9975-3269
authors.initials: AJ
authors.lastname: Fairbanks
mesh_terms: D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D000073893:Sugars / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014867:Water / Q000737:chemistry*
chemical_list: D006001:Glycoconjugates; D011134:Polysaccharides; D000073893:Sugars; D013438:Sulfhydryl Compounds; D014867:Water