Synthetic approach towards sulfated chondroitin di-, tri- and tetrasaccharides corresponding to the repeating unit.
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 beta GalNAc-(1-->4)-beta GlcA 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 [beta GalN3-(1-->4)-beta GlcA2] sequence.
Tamura
J
J
Institute of Physical and Chemical Research (RIKEN), Saitama, Japan.
Neumann
K W
KW
Kurono
S
S
Ogawa
T
T
D002240:Carbohydrate Sequence; D002247:Carbon Isotopes; D002809:Chondroitin Sulfates / Q000138:chemical synthesis*; D004187:Disaccharides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D011522:Protons; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014312:Trisaccharides / Q000138:chemical synthesis*
D002247:Carbon Isotopes; D004187:Disaccharides; D009844:Oligosaccharides; D011522:Protons; D014312:Trisaccharides; D002809:Chondroitin Sulfates