Synthesis and interaction with midkine of biotinylated chondroitin sulfate tetrasaccharides.

Regiospecifically sulfated chondroitin sulfate repeating tetrasaccharides, CS-OO, GlcAß-GalNAcß-GlcAß-GalNAcß;CS-EE, GlcAß-GalNAc(4S6S)ß-GlcAß-GalNAc(4S6S)ß; and CS-AA, GlcAß-GalNAc(4S)ß-GlcAß-GalNAc(4S)ß, having biotin linked with a hydrophilic linker at the reducing terminal were synthesized effectively by a coupling of the corresponding disaccharide units and regioselective sulfation. CS-EE showed greater affinity for midkine than CS-AA and CS-OO.

Amounts and compositional analysis of glycosaminoglycans in the tissue of fish.

We isolated GAGs from the inedible parts; head, skin, internal organs, fins, scales and spine, of atlantic mackerel (Scomber scombrus), japanese jack mackerel (Trachurus japonicus), pacific bluefin tuna (Thunnus orientalis), yellowfin sole (Limanda aspera), broadbanded thornyhead (Sebastolobus macrochir), golden threadfin bream (Nemipterus virgatus), and nile tilapia (Oreochromis niloticus). We also investigated deep-sea fish, eelpouts (Bothrocara hollandi, Lycodes toyamensis, and Lycodes nakamurae), rough snailfish (Careproctus trachysoma), and squids (Watasenia scintillans, Enoploteuthis chunii, and Berryteuthis magister). Enzymatic digestion of the GAGs enabled a compositional analysis of CS, DS, and HA including the sulfation patterns of CS and DS, as well as the amount of each GAG. The molecular weights and distributions of these GAGs were also examined. The amounts of GAGs contained in the tissues and CS/DS ratios differed remarkably among the fish. The dorsal fin of the yellowfin sole contained more than 1300mg of CS-DS per 100g of defatted-dry tissue. Although the fish generally contained A-type rich CS-DS, bottom fish and deep-sea fish often possessed C-type CS-DS in larger ratios. Squid characteristically had E-type CS-DS which was normally less common in fish except in cartilaginous fish. These analytical results had no relation to the biological classification.