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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机译:人血型相关的聚糖抗原是岩藻糖基化的(新)乳糖系列寡糖,在致病过程中起关键作用。 Lewis II型链抗原标记着癌细胞的表面,但同时也是细菌感染的媒介。为了研究路易斯型聚糖的生物学作用,已经开发了许多合成方法。在这里,我们说明了如何使用一组六个单糖构建基块进行的自动聚糖组装(AGA)如何快速访问一系列超过十种已定义的Lewis I型和II型抗原,包括Le x sup> ,Le y sup>,Le a sup>,Le b sup>和KH-1。遵循严格的线性方法组装了具有多达三个α-岩藻糖分支的聚糖,并获得了出色的立体选择性和纯度。
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