Synthetic Organic Chemistry Laboratory

Our laboratory focuses on the following research areas based on synthetic organic chemistry: 1) development of new reactions and methodologies for the efficient synthesis of bioactive molecules, 2) design and synthesis of molecules having unique biological activity, 3) biological researches using these unique molecules as biological probes. Our research interests encompass from transition metal-catalyzed enantioselective reactions to the design and synthesis of intracellular signal transduction modulators and their application to cell biology research. Design and synthesis of selective inhibitors of protein kinases and phosphatases, which are involved in the signal transduction of cell proliferation, aiming for the clarification of the functions of their target enzymes are of particular interest. Clarification of the unknown molecular mechanism of cell death (necrosis) by using our original cell death control molecules is also currently underway. We are also working on the synthesis of ganglioside analogues and several other natural products having interesting biological activities.

Research Subjects

• Development of novel catalytic enantioselective reactions
• Development of selective inhibitors of protein kinases and phosphatases
• Development of cell death inhibitors and clarification of their molecular mechanism of action
• Development of molecular probes for clarification of gangliosides
• Development of new chemical method for the chemical biology research

Publications

1. Ayako Tsuchiya, Miwako Asanuma, Go Hirai, Kana Oonuma, Muhammad Muddassar, Eri Nishizawa, Yusuke Koyama, Yuko Otani, Kam Y. J. Zhang, and Mikiko Sodeoka:
   "CDC25A-inhibitory RE Derivatives Bind to Pocket Adjacent to the Catalytic Site"
   Mol. BioSyst. in press (DOI:10.1039/C3MB00003F)
2. Hiromichi Egami, Ryo Shimizu, Shintaro Kawamura, and Mikiko Sodeoka:
   "Alkene Trifluoromethylation Coupled with C-C Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles"
   Angew. Chem. Int. Ed. in press (DOI:10.1002/anie.201210250)
3. Hiroyuki Yamakoshi, Kosuke Dodo, Masaya Okada, Jun Ando, Almar Palonpon, Katsumasa Fujita, Satoshi Kawata, and Mikiko Sodeoka:
   "Alkyne-tag Raman imaging for visualization of mobile small molecules in live cells"
   J. Am. Chem. Soc. 134, 20681-20689 (2012)
4. Masaki Morita, Go Hirai, Meguni Ohkubo Hiroyuki koshino, Daisuke Hashizume, Keiji Maruoka, and Mikiko Sodeoka:
   "Kinetically Controlled One-Pot Formation of DEFGH-Rings of Type B Physalins through Domino-Type Transformations"
   Org. Lett, 14, 3434-3437 (2012)
5. Shoko Suzuki, Yuki Kitamura, Sylvain Lectard, Yoshitaka Hamashima, Mikiko Sodeoka:
   "Catalytic Asymmetric Mono-Fluorination of a-Keto Esters: Synthesis of Optically Active b-Fluoro-a-Hydroxy and b-Fluoro-a-Amino Acid Derivatives "
   Angew. Chem. Int. Ed. 51, 4581-4585 (2012)
6. Ryo Shimizu, Hiromichi Egami, Yoshitaka Hamashima, Mikiko Sodeoka:
   "Copper-Catalyzed Trifluoromethylation of Allylsilanes"
   Angew. Chem. Int. Ed. 51, 4577-4580 (2012)
7. Ayako Tsuchiya, Go Hirai, Yusuke Koyama, Kana Oonuma, Yuko Otani, Hiroyuki Osada, and Mikiko Sodeoka:
   "Dual-specificity Protein Phosphatase CDC25A/B Inhibitor Identified from a Focused Library with Non-electrophilic Enamine Core Structure"
   ACS Med. Chem. Lett. 3, 294-298 (2012)
8. Hiromichi Egami, Shinji Kamisuki, Kosuke Dodo, Miwako Asanuma, Yoshitaka Hamashima and Mikiko Sodeoka:
   "Catch & release of alkyne-tagged molecules in water by polymer-supported cobalt complex"
   Org. Biomol. Chem. 9, 7667-7670 (2011)
9. Hiroyuki Yamakoshi, Kosuke Dodo, Masaya Okada, Jun Ando, Almar Palonpon, Katsumasa Fujita, Satoshi Kawata, and Mikiko Sodeoka:
   "Imaging of EdU, an Alkyne-Tagged Cell Proliferation Probe, by Raman Microscopy"
   J. Am. Chem. Soc. 133, 6102-6105 (2011)
10. Go Hirai, Ayako Tsuchiya, Yusuke Koyama, Yuko Otani, Kana Oonuma, Kosuke Dodo, Siro Simizu, Hiroyuki Osada, and Mikiko Sodeoka:
    "Development of a Vaccinia H1-Related (VHR) Phosphatase Inhibitor with a NonAcidic Phosphate-Mimicking Core Structure"
    ChemMedChem, 6, 617-622 (2011)