title: Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages.
abstract: Automated glycan assembly (AGA) has advanced from a concept to a commercial technology that rapidly provides access to diverse oligosaccharide chains as long as 30-mers. To date, AGA was mainly employed to incorporate trans-glycosidic linkages, where C2 participating protecting groups ensure stereoselective couplings. Stereocontrol during the installation of cis-glycosidic linkages cannot rely on C2-participation and anomeric mixtures are typically formed. Here, we demonstrate that oligosaccharides containing multiple cis-glycosidic linkages can be prepared efficiently by AGA using monosaccharide building blocks equipped with remote participating protecting groups. The concept is illustrated by the automated syntheses of biologically relevant oligosaccharides bearing various cis-galactosidic and cis-glucosidic linkages. This work provides further proof that AGA facilitates the synthesis of complex oligosaccharides with multiple cis-linkages and other biologically important oligosaccharides.
authors: Department of Bimolecular System, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, Potsdam 14424, Germany.|Institute of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, Berlin 14195, Germany.
authors: Heung Sik
authors: http://orcid.org/0000-0003-2326-7923
authors: HS
authors: Hahm
authors: Department of Bimolecular System, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, Potsdam 14424, Germany.
authors: Mattan
authors: M
authors: Hurevich
authors: Department of Bimolecular System, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, Potsdam 14424, Germany.|Institute of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, Berlin 14195, Germany.
authors: Peter H
authors: PH
authors: Seeberger
mesh_terms: D057205:Automation, Laboratory / Q000379:methods; D005697:Galactosides / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry*; D006031:Glycosylation; D009005:Monosaccharides / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D005697:Galactosides; D005960:Glucosides; D009005:Monosaccharides; D009844:Oligosaccharides