title: Synthesis of phosphorylated and sulfated glycosyl serines in the linkage region of the glycosaminoglycans.
abstract: We synthesized novel acidic glycans having acidic groups located in the linkage region of the glycosaminoglycans (GAGs). The targeted compounds, beta-D-Xyl(2P)-Ser (1), beta-D-Gal(+/-6S)-(1-->4)-beta-D-Xyl(2P)-Ser (3 and 2), beta-D-Gal(+/-6S)-(1-->3)-beta-D-Gal-(1-->4)-beta-D-Xyl(2P)-Ser (5 and 4), and beta-D-Gal-(1-->3)-beta-D-Gal(6S)-(1-->4)-beta-D-Xyl(2P)-Ser (6) contain phosphate and/or sulfate at the specified positions. Some of them (3, 5, and 6) are the first synthesized examples of natural-type glycoconjugates that simultaneously possess phosphate and sulfate as well as carboxylic acid.
authors.affiliation: Department of Environmental Sciences, Faculty of Education & Regional Sciences, Tottori University, Tottori, 680-8551 Japan. jtamura@fed.tottori-u.ac.jp
authors.forename: J
authors.initials: J
authors.lastname: Tamura
authors.forename: J
authors.initials: J
authors.lastname: Nishihara
mesh_terms: D002240:Carbohydrate Sequence; D006025:Glycosaminoglycans / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006025:Glycosaminoglycans; D007202:Indicators and Reagents; D009844:Oligosaccharides; D012694:Serine