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Journal Article

Automated glycan assembly of Lewis type I and II oligosaccharide antigens

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Guberman,  Mónica
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Bräutigam,  Maria
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Guberman, M., Bräutigam, M., & Seeberger, P. H. (2019). Automated glycan assembly of Lewis type I and II oligosaccharide antigens. Chemical Science, 10(21), 5634-5640. doi:10.1039/c9sc00768g.


Cite as: https://hdl.handle.net/21.11116/0000-0004-6271-E
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 Lex, Ley, Lea, Leb and KH-1. Glycans with up to three
a-fucose branches were assembled following a strictly linear approach and obtained in excellent
stereoselectivity and purity.