Synthesis of linear-type chondroitin clusters having a C8 spacer between disaccharide moieties and enzymatic transfer of D-glucuronic acid to the artificial glycans.
Newly designed linear-type glycoclusters were synthesized which involve a chondroitin repeating disaccharide ligand and a hydrophobic octyl ether spacer. The spacer mimics the corresponding disaccharide unit. Repeating elongation of the pseudo-tetrasaccharide that was derived from the common cluster unit [-->8)-octyl-(1-->3)-beta-D-Gal-NAc-(1-->4)-beta-D-GlcA-(1-->] allowed the syntheses of up to the pseudo-decasaccharide analog of chondroitin. An enzymatic D-GlcA transfer at the non-reducing end of the synthesized artificial glycans by GlcATase II was observed.
Tamura
J
J
Department of Environmental Sciences, Faculty of Education and Regional Sciences, Tottori University, Japan. jtamura@fed.tottori-u.ac.jp
Urashima
H
H
Tsuchida
K
K
Kitagawa
H
H
Sugahara
K
K
D002240:Carbohydrate Sequence; D002807:Chondroitin / Q000737:chemistry*; D004187:Disaccharides / Q000737:chemistry*; D005944:Glucosamine; D020723:Glucuronic Acid / Q000378:metabolism*; D014453:Glucuronosyltransferase / Q000378:metabolism*; D008969:Molecular Sequence Data; D000442:Octanols / Q000737:chemistry*
D004187:Disaccharides; D000442:Octanols; D020723:Glucuronic Acid; D002807:Chondroitin; D014453:Glucuronosyltransferase; D005944:Glucosamine