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

Abstract

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.