Department of Chemistry, Temple University , Philadelphia, Pennsylvania 19122, United States.
J Am Chem Soc. 2016 May 11;138(18):5833-6. doi: 10.1021/jacs.6b03373. Epub 2016 Apr 28.
Promysalin is a species-specific Pseudomonad metabolite with unique bioactivity. To better understand the mode of action of this natural product, we synthesized 16 analogs utilizing diverted total synthesis (DTS). Our analog studies revealed that the bioactivity of promysalin is sensitive to changes within its hydrogen bond network whereby alteration has drastic biological consequences. The DTS library not only yielded three analogs that retained potency but also provided insights that resulted in the identification of a previously unknown ability of promysalin to bind iron. These findings coupled with previous observations hint at a complex multifaceted role of the natural product within the rhizosphere.
普罗美沙林是一种具有独特生物活性的种特异性假单胞菌代谢物。为了更好地了解该天然产物的作用模式，我们利用定向总合成（DTS）合成了 16 种类似物。我们的类似物研究表明，普罗美沙林的生物活性对其氢键网络内的变化很敏感，这种变化会产生巨大的生物学后果。DTS 文库不仅产生了三种保留效力的类似物，还提供了深入的见解，从而确定了普罗美沙林以前未知的结合铁的能力。这些发现以及之前的观察结果表明，该天然产物在根际中具有复杂的多方面作用。
