Selectivity and mechanistic inquiries into the reactivity of pericosine A, an electrophilic chlorinated shikimate analogue

Microorganisms are constantly competing for limited resources in their environment as characterized by secondary metabolite production and enzymatic inactivation of toxins. Pericosine A, a shikimate analogue produced by a Tolypocladium sp., has been shown to directly differentiate and inactivate nucleophilic toxins in complex chemical environments. Herein we detail the selectivity of pericosine A towards a diverse set of nucleophiles, as well as the computational and structural studies of the mechanistic pathways under which it operates. We also show reactivity of pericosine A adducts with monosaccharides to produce novel heterobicyclic scaffolds.