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.
|Translated title of the contribution||Synthesis and Conversion of Bongkrekic Acid and its Bioactivity|
|Number of pages||13|
|Journal||Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry|
|Publication status||Published - 2022|
All Science Journal Classification (ASJC) codes
- Organic Chemistry