小分子探针2-叠氮乙酰氨基-1,3,4,6-四乙酰基葡萄糖的合成

Total Synthesis of 1,3,4,6-tetra-acetyl-2-deoxy-2-azide-Glucosamine

实验以氨基葡萄糖盐酸盐为起始原料,经过一系列反应(共5步)得到目标产物6,其可作为非天然小分子探针代谢标记O-GlcNAc糖基化蛋白。在步骤3的丙酮、浓盐酸、50℃条件下分离得到一种具有荧光性能的中间体7,并通过核磁、质谱等检测方法确定其结构,同时探讨了其生成机理。

In this paper,we used the commercially available Glucosamine hydrochloride as starting material,totally five steps,to synthesize target product 6,which can be used as unnatural small molecular probe for metabolically labeling O-GlcNAc modified proteins in mammal cells.In the condition of acetone,concentrated HCl at 50℃in step 3,we discovered an interesting byproduct 7 with strong fluorescence,the structure of which was further confirmed with NMR and MS,and the plausible mechanism was also explored.