Synthesis of phosphorylated and sulfated glycosyl serines in the linkage region of the glycosaminoglycans.
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.
Tamura
J
J
Department of Environmental Sciences, Faculty of Education & Regional Sciences, Tottori University, Tottori, 680-8551 Japan. jtamura@fed.tottori-u.ac.jp
Nishihara
J
J
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
D006025:Glycosaminoglycans; D007202:Indicators and Reagents; D009844:Oligosaccharides; D012694:Serine