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.
Highlights
Lewis antigens are lacto- or neolacto-series oligosaccharides that are commonly found as part of glycoproteins or glycolipids on the eukaryotic cell surface.[1,2,3] These antigens are related to the ABO blood-group system and are implicated in developmental processes, reproductive physiology, oncogenic transformations, cell–cell communication and pathogen–host interactions.[2,4,5,6,7,8,9,10,11] Lewis lacto-series glycans 1–3 are fucosylated versions of a lactotetraosyl (Lc4) core 4
Lewis type-II-chain antigens mark the surface of cancer cells, but are mediators of bacterial infections
Type-II chain analogue Lewisy (Ley) 7 is a tumor-associated carbohydrate antigen (TACA), that is overexpressed on the cell surface of several types of cancer.[12,13,14]
Summary
Sci., 2019, 10, 5634 All publication charges for this article have been paid for by the Royal Society of Chemistry. 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 mediators of bacterial infections. To investigate the biological roles of Lewis type glycans a host of synthetic approaches has been developed. 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
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
