Efforts toward the synthesis of NA22598A1 and the investigation of its mechanism of action

NA22598A1 is a unique carbamoylated cyclic guanidine with a diol skipped diamine dipeptide. It was shown to have antimetastatic activity against DLD-1 colon cancer cells with an IC50 of 0.32 µM, but the absolute stereochemistry has yet to be confirmed. Guadinomine B is also a carbamoylated cyclic guanidine with a diol skipped diamine dipeptide. It was shown to inhibit the T3SS virulence system of Gram-negative bacteria with an IC50 of 0.014 µM. We endeavored to synthesize NA22598A1 and determine if it was mischaracterized at isolation. In addition, we investigated a potential mechanism of action that could produce both of the phenotypes exhibited by NA22598A1 and guadinomine B.