title: Efficient and stereocontrolled synthesis of chondroitin mono- and disaccharide linked to variously sulfated biotinylated trisaccharides of the linkage region of proteoglycans.
abstract: Efficient and stereocontrolled preparation of a library of variously sulfated biotinylated tetra- and pentasaccharides possessing the backbone of the partial linkage region plus the first chondroitin sulfate mono- or disaccharide unit (d-GlcA)n-β-d-(1,3)-GalNAc-β-d-(1,4)-GlcA-β-d-(1,3)-Gal-β-d-(1,3)-Gal (n = 0 or 1) is reported herein for the first time. The synthesis of these compounds was achieved using common key intermediates and a disaccharide building block obtained by semisynthesis. Stereoselective glycosylation, selective protection/deprotection steps, efficient reduction of the N-trichloroacetyl group into the corresponding N-acetyl group, efficient sulfation strategy, deprotection and biotinylation afforded target oligomers in good yield with high purity.
authors: Univ. Orléans et CNRS, ICOA, UMR 7311, F-45067, France. chrystel.lopin-bon@univ-orleans.fr.
authors: Katia
authors: K
authors: Aït-Mohand
authors: Univ. Orléans et CNRS, ICOA, UMR 7311, F-45067, France. chrystel.lopin-bon@univ-orleans.fr.
authors: Anaïs
authors: A
authors: Mirault
authors: Univ. Orléans et CNRS, ICOA, UMR 7311, F-45067, France. chrystel.lopin-bon@univ-orleans.fr.
authors: Jean-Claude
authors: JC
authors: Jacquinet
authors: Univ. Orléans et CNRS, ICOA, UMR 7311, F-45067, France. chrystel.lopin-bon@univ-orleans.fr.
authors: Chrystel
authors: C
authors: Lopin-Bon
mesh_terms: D019921:Biotinylation; D002236:Carbohydrate Conformation; D002807:Chondroitin / Q000737:chemistry*; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011509:Proteoglycans / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009005:Monosaccharides; D009844:Oligosaccharides; D011509:Proteoglycans; D002807:Chondroitin