Synthesis, structural, and biological activity of oligomers derived from muco-inositol and conduritol F

A chemo enzymatic synthesis of novel inositol oligomers is reported. The starting material used for the preparation of all oligomers was obtained by whole-cell fermentation of bromobenzene with E. coli JM109 (pDTG601). Using an iterative methodology, the key sequence was the coupling of homochiral vinyloxiranes in a regio- and stereo-controlled fashion to furnish inositol and conduritol oligomers. With this strategy, repetition of the initial coupling to build higher order oligomers was prepared. A significant step presented in this synthetic route consisted of a selective electrochemical reduction of a vinyl bromide in the presence of cinnamyl ether. All compounds were fully characterized and evaluated for their inhibitory properties against six commercially available glycosidase.