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Org Lett. 2013 Sep 20;15(18):4678-81. doi: 10.1021/ol401975z. Epub 2013 Sep 4.

Aogacillins A and B produced by Simplicillium sp. FKI-5985: new circumventors of arbekacin resistance in MRSA.

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Faculty of Pharmaceutical Sciences, Tokyo University of Science , 2641 Yamazaki, Noda, Chiba, 278-8510, Japan, Kitasato Institute for Life Sciences, Kitasato University , 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan, School of Pharmacy, Kitasato University , 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan, and Hall-Atwater Laboratories of Chemistry, Wesleyan University , Middletown, Connecticut 06459-0180, United States.


Aogacillins A and B, capable of overcoming arbekacin resistance in methicillin-resistant Staphylococcus aureus (MRSA), were isolated from a culture broth of Simplicillium sp. FKI-5985. Their structures were elucidated by NMR spectroscopic studies and ECD analyses. The aogacillins possessed a novel carbon skeleton, including a β-keto-γ-methyliden-δ-lactone ring connected to a 2-ethyl-6-methylcyclohexane ring by spiro conjugation.

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