title: Stereoselective synthesis of L-guluronic acid alginates.
abstract: The glycosylation properties of gulopyranosides have been mapped out, and it is shown that gulose has an intrinsic preference for the formation of 1,2-cis-glycosidic bonds. It is postulated that this glycosylation behaviour originates from nucleophilic attack at the oxacarbenium ion, which adopts the most favourable 3H4 conformation. Building on the stereoselectivity of gulose, a guluronic acid alginate trisaccharide was assembled for the first time by using gulopyranosyl building blocks.
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: Leendert J
authors.initials: LJ
authors.lastname: van den Bos
authors.forename: Wouter F J
authors.initials: WF
authors.lastname: Hogendorf
authors.forename: Gerrit
authors.initials: G
authors.lastname: Lodder
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: D000464:Alginates / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006031:Glycosylation; D006603:Hexuronic Acids / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000464:Alginates; D004952:Esters; D006603:Hexuronic Acids; C007896:guluronic acid; D005947:Glucose