title: Stereocontrolled preparation of biotinylated chondroitin sulfate E di-, tetra-, and hexasaccharide conjugates.
abstract: The synthesis of biotinylated conjugates of oligomers of the basic repeating unit of chondroitin sulfate E (CS-E) with the sequence [GlcA-4,6-disulfated GalNAc]n is reported herein for the first time. An efficient and stereocontrolled preparation of di-, tetra-, and hexasaccharide derivatives was achieved using a common key disaccharide intermediate in an iterative way. An unexpected and never reported side reaction on the carbonyl group of the levulinate ester was observed during a coupling reaction. These complex molecules should be useful to study their interactions with various proteins.
authors.affiliation: Institut de Chimie Organique et Analytique, UMR 7311 CNRS et Université d'Orléans, LabEx «SynOrg», Pôle de Chimie, Université d'Orléans, BP 6759, 45067 Orléans Cedex2, France. Electronic address: Jean-Claude.Jacquinet@univ-orleans.fr.
authors.forename: Jean-Claude
authors.initials: JC
authors.lastname: Jacquinet
authors.affiliation: Institut de Chimie Organique et Analytique, UMR 7311 CNRS et Université d'Orléans, LabEx «SynOrg», Pôle de Chimie, Université d'Orléans, BP 6759, 45067 Orléans Cedex2, France.
authors.forename: Chrystel
authors.initials: C
authors.lastname: Lopin-Bon
mesh_terms: D019921:Biotinylation; D002809:Chondroitin Sulfates / Q000737:chemistry*; D004187:Disaccharides / Q000737:chemistry*; D006900:Hydroxylation; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D004187:Disaccharides; D002809:Chondroitin Sulfates
keywords: Biotinylated sugars; Oligosaccharides; Proteoglycans; Sulfoforms