Structural studies on sulfated oligosaccharides derived from the carbohydrate-protein linkage region of chondroitin 6-sulfate proteoglycans of shark cartilage. I. Six compounds containing 0 or 1 sulfate and/or phosphate residues.
Shark cartilage proteoglycans bear predominantly chondroitin 6-sulfate. After exhaustive protease digestion, reductive beta-elimination, and subsequent chondroitinase ABC digestion, 13 hexasaccharide alditols, which are nonsulfated, sulfated, and/or phosphorylated, were obtained from the carbohydrate-protein linkage region. Six compounds, containing 0 or 1 sulfate and/or phosphate residue, represent approximately 40% of the isolated linkage hexasaccharide alditols. They were analyzed by chondroitinase ACII or alkaline phosphatase digestion in conjunction with high performance liquid chromatography, and by 500 MHz one- and two-dimensional 1H NMR spectroscopy. All six compounds have the conventional structure in common. Delta 4,5-GlcA beta 1-3GalNAc beta 1-4GlcA beta 1-3Gal beta 1-3Gal beta 1-4Xyl-ol One compound has no sulfate nor phosphate. Two of the monosulfated compounds have a O-sulfate on C-6 or on C-4 of the GalNAc residue. The third monosulfated compound has a novel O-sulfate on C-6 of the Gal residue attached to xylitol. The two phosphorylated compounds have O-phosphate on C-2 of Xyl-ol, and one of them has in addition sulfate on C-6 of GalNAc.
Sugahara
K
K
Department of Biological Chemistry, Faculty of Pharmaceutical Sciences, Kyoto University, Japan.
Ohi
Y
Y
Harada
T
T
de Waard
P
P
Vliegenthart
J F
JF
D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002356:Cartilage / Q000737:chemistry*; D011508:Chondroitin Sulfate Proteoglycans / Q000737:chemistry* / Q000302:isolation & purification; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D004187:Disaccharides / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry* / Q000302:isolation & purification; D010457:Peptidoglycan / Q000737:chemistry* / Q000302:isolation & purification; D010710:Phosphates / Q000032:analysis; D012754:Sharks; D013464:Sulfuric Acids / Q000032:analysis
D011508:Chondroitin Sulfate Proteoglycans; D004187:Disaccharides; D009844:Oligosaccharides; D010457:Peptidoglycan; D010710:Phosphates; D013464:Sulfuric Acids