title: The application of 2,2,2-trichloroethyl sulfate to the synthesis of chondroitin sulfate C and D.
abstract: Chondroitin sulfates (CSs) have characteristic bioactivities that depend on sulfation patterns. Chemically synthesized CS oligosaccharides are valuable tools for elucidating the relationship between structures and bioactivities. 2,2,2-Trichloroethyl (TCE) sulfated sugars are highly soluble in nonpolar solvents, which is useful for the synthesis of sulfated oligosaccharides. We herein synthesized CS-C [βGalNAc6S(1-4)βGlcA] (1) and CS-D [βGalNAc6S(1-4)βGlcA2S] (2) disaccharides that possessed sulfate groups by TCE sulfation at O-6 of GalNAc and an additional sulfate group at O-2 of GlcA, respectively. We revealed the superior functionalities of TCE sulfates during the synthesis of CS-C and -D, despite the unwanted side reactions in the acetamido-containing substrate.
authors: Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, Koyamacho-Minami 4-101, Tottori 680-8552, Japan.
authors: Kenya
authors: K
authors: Matsushita
authors: Department of Regional Environment, Faculty of Regional Sciences, Tottori University, Koyamacho-Minami 4-101, Tottori 680-8551, Japan.
authors: Tomomi
authors: T
authors: Nakata
authors: 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. Electronic address: jtamura@rs.tottori-u.ac.jp.
authors: Jun-ichi
authors: J
authors: Tamura
mesh_terms: D000107:Acetylation; D002809:Chondroitin Sulfates / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013463:Sulfuric Acid Esters / Q000737:chemistry*
chemical_list: D013463:Sulfuric Acid Esters; D002809:Chondroitin Sulfates
keywords: Glycan synthesis; Protected sulfate; Sulfated oligosaccharide