Key Laboratory of Chemical Biology of Natural Products (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan, Shandong 250012, People's Republic of China.
Key Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao, Shandong 266003, People's Republic of China.
Org Lett. 2024 Sep 13;26(36):7739-7743. doi: 10.1021/acs.orglett.4c02897. Epub 2024 Sep 4.
We present the application of -difluoroacetylglucosamine (GlcNDFA) in a chemical evolution strategy to synthesize oligosaccharides. In comparison to conventional -trifluoroacetylglucosamine, GlcNDFA exhibits superior substrate compatibility with glycosyltransferases as well as stability in aqueous environments. Using our 16-step assembly line, GlcNDFA can be used to produce homogeneous dekaparin, a heparin-like medication, with a yield of 62.2%. This underscores the significant potential of GlcNDFA as a chemical evolution precursor in the precise synthesis of structurally defined polysaccharides.
我们展示了 -二氟乙酰氨基葡萄糖（GlcNDFA）在化学进化策略中的应用，用于合成寡糖。与传统的 -三氟乙酰氨基葡萄糖相比，GlcNDFA 与糖基转移酶具有更好的底物兼容性，并且在水相环境中稳定。使用我们的 16 步组装线，GlcNDFA 可以用于生产产率为 62.2%的均一的去硫酸肝素，一种类似肝素的药物。这突显了 GlcNDFA 作为化学进化前体在结构确定的多糖精确合成中的巨大潜力。
