Automated glycan assembly of Lewis type I and II oligosaccharide antigens

Mónica Guberman; Maria Bräutigam; Peter H Seeberger

doi:10.1039/c9sc00768g

Automated glycan assembly of Lewis type I and II oligosaccharide antigens

Chem Sci. 2019 Apr 29;10(21):5634-5640. doi: 10.1039/c9sc00768g. eCollection 2019 Jun 7.

Authors

Mónica Guberman^{1

2}, Maria Bräutigam¹, Peter H Seeberger^{1

2}

Affiliations

¹ Department of Biomolecular Systems , Max Planck Institute of Colloids and Interfaces , Am Mühlenberg 1 , 14476 Potsdam , Germany . Email: Peter.Seeberger@mpikg.mpg.de.
² Department of Chemistry and Biochemistry , Freie Universität Berlin , Arnimalle 22 , 14195 Berlin , Germany.

Abstract

Human blood group related glycan antigens are fucosylated (neo-)lactoseries oligosaccharides that play crucial roles in pathogenic processes. Lewis type-II-chain antigens mark the surface of cancer cells, but are also mediators of bacterial infections. To investigate the biological roles of Lewis type glycans a host of synthetic approaches has been developed. Here, we illustrate how automated glycan assembly (AGA) using a set of six monosaccharide building blocks provides quick access to a series of more than ten defined Lewis type-I and type-II antigens, including Le^x, Le^y, Le^a, Le^b and KH-1. Glycans with up to three α-fucose branches were assembled following a strictly linear approach and obtained in excellent stereoselectivity and purity.