Synthesis of chondroitin sulfate CC and DD tetrasaccharides and interactions with 2H6 and LY111. Issue 5 (1st March 2018)

• Record Type: Journal Article
• Authors: Matsushita, Kenya; Nakata, Tomomi; Takeda-Okuda, Naoko; Nadanaka, Satomi; Kitagawa, Hiroshi; Tamura, Jun-ichi
• Is Part Of: Bioorganic & medicinal chemistry. Volume 26:Issue 5(2018)
• Page Start: 1016
• Page End: 1025
• Publication Date: 2018-03-01
• Subjects: CS chondroitin sulfate -- GlcA d-glucuronic acid -- GalNAc N-acetyl-d-galactosamine -- MS molecular sieves -- TMSOTf trimethylsilyl triflate -- NAP (2-naphtyl)methyl -- DDQ 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone -- MBz 4-methylbenzoyl -- Z benzyloxycarbonyl; Chondroitin sulfate -- Glycosylation -- Oligosaccharide synthesis -- 2H6 -- LY111; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2018.01.011
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: 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.