Syntheses of chondroitin sulfate tetrasaccharide structures containing 4,6-disulfate patterns and analysis of their interaction with glycosaminoglycan-binding protein

Kento Miyachi; Masahiro Wakao; Yasuo Suda

doi:10.1016/j.bmcl.2015.02.011

Syntheses of chondroitin sulfate tetrasaccharide structures containing 4,6-disulfate patterns and analysis of their interaction with glycosaminoglycan-binding protein

Bioorg Med Chem Lett. 2015 Apr 1;25(7):1552-5. doi: 10.1016/j.bmcl.2015.02.011. Epub 2015 Feb 16.

Authors

Kento Miyachi¹, Masahiro Wakao², Yasuo Suda³

Affiliations

¹ Department of Chemistry, Biotechnology, and Chemical Engineering, Graduate School of Science and Engineering, Kagoshima University, 1-21-40 Kohrimoto, Kagoshima 890-0065, Japan.
² 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.
³ 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.

PMID: 25752983
DOI: 10.1016/j.bmcl.2015.02.011

Abstract

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).

Keywords: Basic fibroblast growth factor; Chondroitin sulfate; Glycosaminoglycan; Sugar chips; Surface plasmon resonance; Synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Conformation
Chondroitin Sulfates / chemical synthesis
Chondroitin Sulfates / chemistry*
Fibroblast Growth Factors / chemistry*
Glycosaminoglycans / chemistry*
Molecular Sequence Data
Sulfuric Acids / chemistry*
Surface Plasmon Resonance

Substances

Glycosaminoglycans
Sulfuric Acids
Fibroblast Growth Factors
Chondroitin Sulfates