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Development of a one-pot glycosylation method for the synthesis of MMP precursors
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A one-pot glycosylation method was developed to simplify the synthesis of precursors of 3-O-methyl-mannose polysaccharides (MMPs) required for biosynthetic studies on mycobacteria. The unusual intracellular polysaccharides, proposed to modulate the formation of important building blocks for components of their cell wall, could uncover new and effective treatments against these threatening drug-resistent pathogens. Reacting trichloroacetyl and Ntrichloroacetylcarbamate donor mannosides of temperature controlled reactivity, allowed the synthesis of the desired trimannoside (26%) with an estimated aa-selectivity greater than 99%, under activation by the same Lewis acid. Although the problem of enhancing both reactivity and selectivity still remains to address, interesting promising solutions are proposed which have the potential to be developed as an approach to a viable new method to supply larger MMPs synthetic targets. Furthermore, the scope of these less commonly used leaving groups as well the applications of the presented protecting strategies for combined donor and acceptor glycosides, essential for the synthesis of other oligo and polysaccharides, are discussed.
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mycobacteria MMPs one-pot reaction glycosylation trisaccharide