Synthesis of chondroitin sulfate CC and DD tetrasaccharides and interactions with 2H6 and LY111

Kenya Matsushita; Tomomi Nakata; Naoko Takeda-Okuda; Satomi Nadanaka; Hiroshi Kitagawa; Jun-Ichi Tamura

doi:10.1016/j.bmc.2018.01.011

Synthesis of chondroitin sulfate CC and DD tetrasaccharides and interactions with 2H6 and LY111

Bioorg Med Chem. 2018 Mar 1;26(5):1016-1025. doi: 10.1016/j.bmc.2018.01.011. Epub 2018 Feb 3.

Authors

Kenya Matsushita¹, Tomomi Nakata², Naoko Takeda-Okuda³, Satomi Nadanaka⁴, Hiroshi Kitagawa⁴, Jun-Ichi Tamura⁵

Affiliations

¹ Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, Koyamacho-Minami 4-101, Tottori 680-8552, Japan.
² Department of Regional Environment, Faculty of Regional Sciences, Tottori University, Koyamacho-Minami 4-101, Tottori 680-8551, Japan.
³ Department of Life and Environmental Agricultural Sciences, Faculty of Agriculture, Tottori University, Koyamacho-Minami 4-101, Tottori 680-8553, Japan.
⁴ Department of Biochemistry, Kobe Pharmaceutical University, Higashinada-ku, Kobe 658-8558, Japan.
⁵ Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, Koyamacho-Minami 4-101, Tottori 680-8552, Japan; Department of Regional Environment, Faculty of Regional Sciences, Tottori University, Koyamacho-Minami 4-101, Tottori 680-8551, Japan; Department of Life and Environmental Agricultural Sciences, Faculty of Agriculture, Tottori University, Koyamacho-Minami 4-101, Tottori 680-8553, Japan. Electronic address: jtamura@muses.tottori-u.ac.jp.

PMID: 29402610
DOI: 10.1016/j.bmc.2018.01.011

Abstract

We synthesized the biotinylated chondroitin sulfate tetrasaccharides CS-CC [-3)βGalNAc6S(1-4)βGlcA(1-]₂ and CS-DD [-3)βGalNAc6S(1-4)βGlcA2S(1-]₂ which possess sulfate groups at O-6 of GalNAc and an additional sulfate group at O-2 of GlcA, respectively. We also analyzed interactions among CS-CC and CS-DD and the antibodies 2H6 and LY111, both of which are known to bind with CS-A, while CS-DD was shown for the first time to bind with both antibodies.

Keywords: 2H6; Chondroitin sulfate; Glycosylation; LY111; Oligosaccharide synthesis.

Publication types

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

MeSH terms

Antibodies, Monoclonal / immunology*
Biotinylation
Carbohydrate Sequence
Chondroitin Sulfates / chemical synthesis
Chondroitin Sulfates / chemistry*
Chondroitin Sulfates / immunology
Enzyme-Linked Immunosorbent Assay
Oligosaccharides / chemistry*

Substances

Antibodies, Monoclonal
Oligosaccharides
Chondroitin Sulfates