Chondroitin sulfate (CS) is a liner polysaccharide consisting of D-glucuronic acid (GlcA) and N-acetyl-D-galactosamine (GalNAc), and its hydroxyl groups are sulfated regiospecifically. CS has contrastive neuroactivities depending on the sulfation patterns. CS-D [bGlcA2S(1-3)bGalNAc6S] and CS-E [bGlcA(1-3)bGalNAc4S6S] promote neuronal growth1,2), while CS-A [bGlcA(1-3)bGalNAc4S] inhibits axonal guidance and growth3). These results were obtained by using naturally occurring CS polysaccharides which contain heterogeneities on sulfation patterns. To avoid and resolve the problems, it is necessary to investigate the interaction between precisely synthesized CSs and neuroregulator proteins.
Based on the synthetic procedure of the biotinylated CS oligosaccharide4), we planned and synthesized the biotinylated CS-D oligosaccharides; [bGalNAc6S(1-4)bGlcA2S]n-Linker-Biotin by coupling of the suitably protected disaccharide units.
References
1) A. M. Clement et al., J. Biol. Chem., 273, 28444-28435 (1998).
2) M. Hikino et al., J. Biol. Chem., 278, 43744-43754 (2003).
3) H. Wang et al., J. Cell Sci., 121, 3083-3091 (2008).
4) J. Tamura et al., Bioorg. Med. Chem. Lett., 22, 1371-1374 (2012).
