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

Translated title of the contribution: Synthesis and Conversion of Bongkrekic Acid and its Bioactivity

Research output: Contribution to journalArticlepeer-review

Abstract

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 contributionSynthesis and Conversion of Bongkrekic Acid and its Bioactivity
Original languageJapanese
Pages (from-to)1136-1148
Number of pages13
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume80
Issue number12
DOIs
Publication statusPublished - 2022

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis and Conversion of Bongkrekic Acid and its Bioactivity'. Together they form a unique fingerprint.

Cite this