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Synthetic approach towards sulfated chondroitin di-, tri- and tetrasaccharides corresponding to the repeating unit
Tamura, Jun-Ichi,Neumann, Klaus W.,Kurono, Sadamu,Ogawa, Tomoya
, p. 43 - 63 (1997)
Chondroitin di-, tri- and tetrasaccharides, as well as their 4-, 6- mono- and 4,6-disulfates as their 4-methoxyphenyl glycosides, were systematically synthesized. Target disaccharides having βGalNAc-(1 → 4)- βGlcA sequences were obtained starting from the corresponding pivotal chondroitin disaccharide precursor. A trisaccharide intermediate, which was synthesized by coupling of glucuronate imidate with a known disaccharide acceptor, was transformed into the sulfated and non-sulfated chondroitin trisaccharides. Chondroitin tetrasaccharide and the corresponding 4- disulfate, 6-disulfate as well as 4,6-tetrasulfate were also obtained based on the strategy developed above starting from the reported tetrasaccharide having [βGalN3-(1 → 4)-βGlcA2] sequence.
