2,3-二乙酰氨基D-甘露糖醛酸的化学合成

Most bacterial cell surface glycans have unique structures and are considered ideal targets for the development of detection and diagnostic techniques as well as vaccines. Chemical synthesis is an effective and accurate method to prepare well-defined oligosaccharides, which provides convenience for exploring the structure-activity relationship of bacterial glycans and biomedical applications. D-aminomannuronic acid is a rare sugar, which exists in the surface polysaccharide of pathogenic bacteria.In this paper, 2,3-diamino-D-mannuronic acid was designed and synthesized.The synthesis strategy based on nucleophilic substitution and TEMPO/BAIB-mediated oxidation of C6 can well convert D-glucose to the corresponding D-aminomannuronic acid.It is worth noting that the efficiency of C1 connecting arm assembly of p-toluene thioside is significantly higher than that of C1 terminal connecting arm assembly of allyl glycoside. In addition, acyl group migration was also found in the study. The chemical synthesis of rare 2,3-diamino-D-mannuronic acid building blocks will provide the basis for the synthesis of complex bacterial glycans.