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Automated glycan assembly of Lewis type I and II oligosaccharide antigens.

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.

SUBMITTER: Guberman M

PROVIDER: S-EPMC6552968 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Automated glycan assembly of Lewis type I and II oligosaccharide antigens.

Guberman Mónica M Bräutigam Maria M Seeberger Peter H PH

Chemical science 20190429 21

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 serie ...[more]

PMID: 31293748

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