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Bioorganic Chemistry

  • Tohru Oishi, Professor
  • Kohei Torikai, Associate Professor
  • Makoto Ebine, Associate Professor
Interesting organic compounds called as natural products isolated from animals, plants, and microorganisms elicit potent biological activities by acting against cell membranes and certain proteins, and utilized as antibiotics and anticancer drugs. Our group studies about structure determination and total synthesis of bioactive natural products, elucidation of their target proteins and mode of action, and chemical biology based on design and synthesis of bioactive molecules.
Keywords: Natural Products, Biosynthesis, Structure Determination, Organic Synthesis, Total Synthesis, Chemical Biology

1. Chemical synthesis of ladder-shaped polyethers and elucidation of mode-of-action:

Maitotoxin, which is associated with Ciguatera seafood poisoning, shows potent cytotoxicity and Ca2+ influx activity at extremely low concentration. To elucidate its target protein and mode-of-action, chemical synthesis of the rare natural product, its analog molecules, and molecular probes are studied.

Figure 1

2. Application of microflow reactor to natural product synthesis

Microflow reactor is a novel device for organic synthesis, which enable to utilize labile intermediates. Applications of microflow reactors for total synthesis of natural products are studied.

3. Structure determination of the membrane acting natural products and development of novel antifungal drugs

The appearance of the resistant bacteria against antibiotics becomes the social problem. Amphidinol 3 (AM3), isolated from dinoflagellate Amphidinium krebsi, shows potent antifungal activity. To confirm the stereochemistry and elucidate the mode-of-action of AM3, chemical synthesis of AM3 and its analogs are studied. Development of novel antifungal drugs based on AM3 is also under investigation.