Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 24, Pages 13643-13648Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02342
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Funding
- National Key Research and Development Program of China [2017YFA0505200]
- National High Technology Project 973 [2015CB856200]
- NNSFC [21472010, 21521003, 21561142002, 21625201]
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Staphylopine was discovered and functionally evaluated as a novel type of metallophore that Staphylococcus 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-beta-lactamases NDM-1 and VIM-2. 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 staphylopine and AMA.
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