Syntheses of chondroitin sulfate tetrasaccharide structures containing 4,6-disulfate patterns and analysis of their interaction with glycosaminoglycan-binding protein.
Chondroitin sulfate tetrasaccharide ligand conjugates, namely GlcA-GalNAc6S-GlcA-GalNAc4S6S (CS-C+E) 1, GlcA2S-GalNAc6S-GlcA2S-GalNAc4S6S (CS-D+T) 2, GlcA-GalNAc4S6S-GlcA-GalNAc4S (CS-E+A) 3, GlcA-GalNAc4S6S-GlcA-GalNAc6S (CS-E+C) 4, and GlcA-GalNAc4S6S-GlcA-GalNAc4S6S (CS-E+E) 5, were systematically synthesized using a disaccharide building block 6. Synthesized CS tetrasaccharide structures were immobilized onto gold-coated chips to prepare array-type sugar chips, and the binding properties of protein were evaluated by surface plasmon resonance imaging biosensor. CS-D+T, CS-E+A, CS-E+C, and CS-E+E showed greater affinity for basic fibroblast growth factor than did other tetrasaccharides (CS-C+D, C+E, D+D).
Department of Chemistry, Biotechnology, and Chemical Engineering, Graduate School of Science and Engineering, Kagoshima University, 1-21-40 Kohrimoto, Kagoshima 890-0065, Japan.
Kento
K
Miyachi
Department of Chemistry, Biotechnology, and Chemical Engineering, Graduate School of Science and Engineering, Kagoshima University, 1-21-40 Kohrimoto, Kagoshima 890-0065, Japan. Electronic address: wakao@eng.kagoshima-u.ac.jp.
Masahiro
M
Wakao
Department of Chemistry, Biotechnology, and Chemical Engineering, Graduate School of Science and Engineering, Kagoshima University, 1-21-40 Kohrimoto, Kagoshima 890-0065, Japan; SUDx-Biotec Corporation, 1-41-1 Shiroyama, Kagoshima 890-0013, Japan. Electronic address: ysuda@eng.kagoshima-u.ac.jp.
Yasuo
Y
Suda
D002236:Carbohydrate Conformation; D002809:Chondroitin Sulfates / Q000138:chemical synthesis / Q000737:chemistry*; D005346:Fibroblast Growth Factors / Q000737:chemistry*; D006025:Glycosaminoglycans / Q000737:chemistry*; D008969:Molecular Sequence Data; D013464:Sulfuric Acids / Q000737:chemistry*; D020349:Surface Plasmon Resonance
D006025:Glycosaminoglycans; D013464:Sulfuric Acids; D005346:Fibroblast Growth Factors; D002809:Chondroitin Sulfates
Basic fibroblast growth factor; Chondroitin sulfate; Glycosaminoglycan; Sugar chips; Surface plasmon resonance; Synthesis