Guadinomines, Type III secretion system inhibitors, produced by streptomyces sp K01-0509

The structures of guadinomines, new inhibitors of a bacterial Type III secretion system produced by Streptomyces sp. KOI-0509, were elucidated by spectroscopic studies including various NMR experiments. Guadinomines A, B, C-1, C-2 and D consist of a carbamoylated cyclic guanidinyl moiety, an alkyl chain moiety and an L-Ala-L-Val moiety in common, while guadinomic acid is a smaller molecule consisting of a carbamoylated cyclic guanidinyl moiety and a hydroxyl hexanoate moiety.