Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages

Heung Sik Hahm, Mattan Hurevich, Peter H. Seeberger*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

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.

Original languageAmerican English
Article number12482
JournalNature Communications
Volume7
DOIs
StatePublished - 1 Sep 2016

Bibliographical note

Funding Information:
We gratefully acknowledge to the Max-Planck Society and the European Research Council (ERC Advanced Grant AUTOHEPARIN) for generous financial support.

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