Automated Glycan Assembly of Complex Oligosaccharides Related to Blood Group Determinants

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• 作者：Heung Sik Hahm ; Chien-Fu Liang ; Chian-Hui Lai ; Richard J. Fair ; Frank Schuhmacher ; Peter H. Seeberger
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：July 15, 2016
• 年：2016
• 卷：81
• 期：14
• 页码：5866-5877
• 全文大小：629K
• 年卷期：0
• ISSN：1520-6904

文摘

Lactotetraosyl (Lc4) and neo-lactotetraosyl (nLc4) are backbones that are common to many glycans. Using automated glycan assembly, these common core structures were constructed and elaborated to access synthetically challenging glycans of biological relevance. The incorporation of α-fucoses is demonstrated for H-type I and II; α(1,3)-galactose epitopes were prepared, and the pentasaccharide HNK-1 required incorporation of a 3-O-sulfate. In addition to preparing the target structures, essential insights were gained regarding the relationships of glycosylating agents and nucleophiles as well as the linker stability.