Zhang, J.; Wang, S.; Bai, Y.; Guo, Q.; Zhou, J.; Lei, X.*
J. Org. Chem. 2017, 82, 13643-13648.
Successful competition for metals by pathogenic bacteria from the host is an important factor in the establishment of a bac-terial infection. Staphylopine was discovered and functionally evaluated as a novel type of metallophore that Staphylococ-cus aureus employs to acquire multiple divalent transition metals. Aspergillomarasmine A (AMA), with a similar structure to staphylopine, was recently identified as an inhibitor of metallo-尾-lactamases NDM-1 and VIM-2, which suggests AMA has a similar metal chelation property as staphylopine. Herein, we report a unified approach using Mitsunobu reaction as a key step to accomplish the concise and efficient total syntheses of staphylopine and AMA. We also elucidate the similar broad-spectrum metal chelation properties between
Successful competition for metals by pathogenic bacteria from the host is an important factor in the establishment of a bac-terial infection. Staphylopine was discovered and functionally evaluated as a novel type of metallophore that Staphylococ-cus aureus employs to acquire multiple divalent transition metals. Aspergillomarasmine A (AMA), with a similar structure to staphylopine, was recently identified as an inhibitor of metallo-尾-lactamases NDM-1 and VIM-2, which suggests AMA has a similar metal chelation property as staphylopine. Herein, we report a unified approach using Mitsunobu reaction as a key step to accomplish the concise and efficient total syntheses of staphylopine and AMA. We also elucidate the similar broad-spectrum metal chelation properties between