title: Automated synthesis of chondroitin sulfate oligosaccharides.
abstract: Glycosaminoglycans (GAGs) are important sulfated carbohydrates prevalently found in the extracellular matrix that serve many biological functions. The synthesis of structurally diverse but defined GAGs is extremely challenging as one has to account for the various sulfation patterns. Described is the automated synthesis of two chondroitin sulfate hexasaccharides. The oligosaccharides are prepared on a solid support that is equipped with a photolabile linker. The linker cleavage from the resin is performed in a continuous-flow photoreactor under chemically mild conditions. The described approach will serve as a general scheme to systematically access oligosaccharides of all GAG families.
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 14, 14476, Potsdam, Germany.
authors.forename: Chien-Fu
authors.initials: CF
authors.lastname: Liang
authors.forename: Heung Sik
authors.initials: HS
authors.lastname: Hahm
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
mesh_terms: D000107:Acetylation; D001331:Automation; D001671:Biochemistry / Q000379:methods*; D002809:Chondroitin Sulfates / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009844:Oligosaccharides; D002809:Chondroitin Sulfates