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Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
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Automated glycan assembly of Lewis type I and II oligosaccharide antigens

Mónica Guberman1,2, Maria Bräutigam1, Peter H Seeberger1,2

  • 1Department of Biomolecular Systems , Max Planck Institute of Colloids and Interfaces , Am Mühlenberg 1 , 14476 Potsdam , Germany .

Chemical Science
|July 12, 2019
PubMed

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 Lex, Ley, Lea, Leb 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.

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