<i>N</i>-Difluoroacetylhexosamine as a Substrate-Engineering Precursor for Glycosylation Reactions
Ya-Lin Cao, Jian-Qun Deng, Yi Li, Si-Yu Xin, Yijing Chen, Xinyu Li, Hongzhi Cao, Xue-Ping Guo, Fengshan Wang, Juzheng Sheng
Abstract
We present the application of N -difluoroacetylglucosamine (GlcNDFA) in a chemical evolution strategy to synthesize oligosaccharides. In comparison to conventional N -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.
Topics & Concepts
ChemistryGlycosylationSubstrate (aquarium)Combinatorial chemistryNanotechnologyBiochemistryMaterials scienceGeologyOceanographyGlycosylation and Glycoproteins ResearchCarbohydrate Chemistry and SynthesisProteoglycans and glycosaminoglycans research