Synthesis and Conversion of Bongkrekic Acid and its Bioactivity

  • Shindo Mitsuru
    Institute for Materials Chemistry and Engineering, Kyushu University
  • Iwata Takayuki
    Institute for Materials Chemistry and Engineering, Kyushu University
  • Kano Arihiro
    Institute for Materials Chemistry and Engineering, Kyushu University
  • Shinohara Yasuo
    Institute for Advanced Medical Sciences, Tokushima University

Bibliographic Information

Other Title
  • アデニンヌクレオチド輸送担体(ANT)阻害剤:ボンクレキン酸の合成とその構造展開および生物活性

Description

<p>Bongkrekic acid (BKA), isolated from the bacterium Burkholderia gladioli, is an inhibitor of adenine nucleotide translocator in the mitochondria inner membrane, and is also a suppressor of apoptosis. Therefore, BKA is an important tool for the investigation of apoptosis as well as mitochondria. Herein, we summarize our total synthesis of BKA and its analogues, and their biological activities. The total synthesis was achieved by employing a three-component convergent strategy based on Julia-Kocienski olefination and Suzuki coupling. Torquoselective olefination with an ynolate was applied for the efficient construction of an unsaturated ester. Based on the total synthesis, various BKA analogues were prepared for structure-activity relationship studies, which indicated that the carboxylic acid moieties were essential for the biological activities of BKA. More readily available BKA analogues with potent biological activity were also developed. A brief summary of the novel biological activities is also provided.</p>

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