Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages

• DOI: 10.1038/ncomms12482
• Publication Date: 2016-09-01T10:48:16Z
• Authors: Heung Sik Hahm; Mattan Hurevich; Peter H Seeberger
• Keywords: Glycosidic bond; Oligosaccharide; Monosaccharide

Automated glycan assembly (AGA) has advanced from a concept to commercial technology that rapidly provides access diverse oligosaccharide chains as long 30-mers. To date, AGA was mainly employed 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 oligosaccharides containing multiple can be prepared efficiently by using monosaccharide building blocks equipped with remote groups. The is illustrated automated syntheses biologically relevant bearing various cis-galactosidic cis-glucosidic linkages. This work further proof facilitates synthesis complex cis-linkages other important oligosaccharides.