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Issue 21, 2019
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Automated glycan assembly of Lewis type I and II oligosaccharide antigens

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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 α-fucose branches were assembled following a strictly linear approach and obtained in excellent stereoselectivity and purity.

Graphical abstract: Automated glycan assembly of Lewis type I and II oligosaccharide antigens

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Publication details

The article was received on 14 Feb 2019, accepted on 27 Apr 2019 and first published on 29 Apr 2019


Article type: Edge Article
DOI: 10.1039/C9SC00768G
Chem. Sci., 2019,10, 5634-5640
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Automated glycan assembly of Lewis type I and II oligosaccharide antigens

    M. Guberman, M. Bräutigam and P. H. Seeberger, Chem. Sci., 2019, 10, 5634
    DOI: 10.1039/C9SC00768G

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