Synthesis of Oligoglucosamine Analogues Containing the N,N,N-Trimethyl-D-glucosaminyl Unit by Automated Electrochemical Assembly (Supporting Information)

Oligosaccharides and polysaccharides containing glucosamine are abundant and essential for many living species, including plants, fungi, insects, and other organisms. TMG-chitotriomycin with the N,N,N-Trimethyl-D-glucosaminyl (TMG) unit shows potent and selective inhibition of insect and fungal GlcNAcases with no inhibition of mammalian and plant GlcNAcases. We have already achieved the total synthesis of TMG-chitotriomycin by automated electrochemical assembly. Thus, we have been interested in synthesis of oligoglucosamine analogues with the TMG unit. Here we synthesized 2- and 3-TMG-chitotriomycin which are analogues of TMG-chitotriomycin and 3-TMG-NAG5 which is a poly N-acetyl glucosamine (PNAG) pentasaccharide analogue.

寡糖和多糖类化合物中含有葡萄糖胺者极为丰富，对于众多生物种类而言，包括植物、真菌、昆虫及其他有机体，均具有不可或缺的重要性。以N,N,N-三甲基-D-葡萄糖胺基（TMG）单元为特征的TMG-壳聚糖素，对昆虫及真菌中的GlcNAcases展现出高效且具有选择性的抑制能力，而对哺乳动物及植物中的GlcNAcases则无抑制作用。我们已通过自动化电化学组装技术实现了TMG-壳聚糖素的完全合成。因此，我们对合成含有TMG单元的寡葡萄糖胺类似物产生了浓厚的兴趣。在本研究中，我们合成了2-和3-TMG-壳聚糖素，它们是TMG-壳聚糖素的类似物，以及3-TMG-NAG5，其为聚N-乙酰葡萄糖胺（PNAG）五糖类似物。