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Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages

Author

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  • Heung Sik Hahm

    (Max Planck Institute of Colloids and Interfaces
    Institute of Chemistry and Biochemistry, Freie Universität Berlin)

  • Mattan Hurevich

    (Max Planck Institute of Colloids and Interfaces
    Present address: Institute of Chemistry, The Hebrew University of Jerusalem, Safra Campus, Givat Ram, 91904 Jerusalem, Israel)

  • Peter H Seeberger

    (Max Planck Institute of Colloids and Interfaces
    Institute of Chemistry and Biochemistry, Freie Universität Berlin)

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.

Suggested Citation

  • Heung Sik Hahm & Mattan Hurevich & Peter H Seeberger, 2016. "Automated assembly of oligosaccharides containing multiple cis-glycosidic linkages," Nature Communications, Nature, vol. 7(1), pages 1-8, November.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms12482
    DOI: 10.1038/ncomms12482
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