Guberman Mónica, Bräutigam Maria, Seeberger Peter H
Department of Biomolecular Systems , Max Planck Institute of Colloids and Interfaces , Am Mühlenberg 1 , 14476 Potsdam , Germany . Email:
Department of Chemistry and Biochemistry , Freie Universität Berlin , Arnimalle 22 , 14195 Berlin , Germany.
Chem Sci. 2019 Apr 29;10(21):5634-5640. doi: 10.1039/c9sc00768g. eCollection 2019 Jun 7.
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, Le, Le, Le 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.
人类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型链抗原标记癌细胞表面，但也是细菌感染的介质。为了研究Lewis型聚糖的生物学作用，已经开发了许多合成方法。在这里，我们展示了如何使用一组六个单糖构建块的自动化聚糖组装（AGA）快速获得一系列十多种定义明确的Lewis I型和II型抗原，包括Le、Le、Le、Le和KH-1。具有多达三个α-岩藻糖分支的聚糖按照严格的线性方法组装，并以优异的立体选择性和纯度获得。
