Chief Scientist Laboratories Synthetic Organic Chemistry Laboratory

Chief Scientist: Mikiko Sodeoka (D.Phar.)

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Research Summary

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 novel synthetic methods using transition metal-catalysts for fluorine-containing molecules and chiral compounds to the design and synthesis of intracellular signal transduction modulators and their application to cell biology research. In particular, we are focusing on enzymes in charge of chemical modification of proteins, such as phosphorylation and methylation. We are working on design and synthesis of selective inhibitors of such enzymes as well as development of new methods for analyzing chemical modification of proteins. Development of new chemical methodology for identification of target protein/binding site of small bioactive molecules and for their imaging. Clarification of the unknown molecular mechanism of cell death (necrosis) by using our original cell death control molecules is also currently underway.

Main Research Fields

Chemistry

Related Research Fields

Biological Sciences
Medicine, Dentistry & Pharmacy
Synthetic Organic Chemistry
Chemical Biology

Keywords

bioactive molecule
catalytic reaction
fluorine-containing molecule

Selected Publications

1. Ezawa, T., Sohtome, Y., Hashizume, D., Adachi, M., Akakabe, M., Koshino, H., and Sodeoka, M.:
"Dynamics in Catalytic Asymmetric Diastereoconvergent (3 + 2) Cycloadditions with Isomerizable Nitrones and α-Keto Ester Enolates"
J. Am. Chem. Soc. 143, 9094-9104 (2021).
2. Hirai, G., Kato, M., Koshino, H., Nishizawa, E., Oonuma, K., Ota, E., Watanabe, T., Hashizume, D., Tamura, Y., Okada, M., Miyagi, T., and Sodeoka, M.:
"Ganglioside GM3 Analogues Containing Monofluoromethylene-linked Sialoside: Synthesis, Stereochemical Effects, Conformational Behavior, and Biological Activities"
JACS Au 1, 137-146 (2021).
3. Sugawara, M., Ohnishi, R., Ezawa, T., Akakabe, M., Sawamura, M., Hojo, D., Hashizume, D., Sohtome,Y., and Sodeoka, M.:
"Regiodivergent Oxidative Cross-Coupling of Catechols with Persistent tert-Carbon Radicals"
ACS Catalysis, 10, 12770-12782 (2020).
4. Dodo, K., Shimizu, T., Sasamori, J., Aihara, K., Terayama, N., Nakao, S., Iuchi, K., Takahashi, M., and Sodeoka, M.:
"Indolylmaleimide Derivative IM-17 Shows Cardioprotective Effects in Ischemia-Reperfusion Injury"
ACS Med. Chem. Lett. 9, 182-187 (2018).
5. Bartlett, S. L., Sohtome, Y., Hashizume, D., White P. S., Sawamura, M., Johnson, J. S., and Sodeoka, M.:
"Catalytic Enantioselective [3+2] Cyclization of α-Keto Ester Enolates and Nitrile Oxides"
J. Am. Chem. Soc. 139, 8661-8666 (2017).
6. Sohtome, Y., Nakamura, G., Muranaka, A., Hashizume, D., Lectard, S., Tsuchimoto, T., Uchiyama, M., and Sodeoka, M.:
"Naked d-Orbital in a Centrochiral Ni(II) Complex as a Catalyst for Asymmetric [3+2] Cycloaddition
Nature Comm. 8, 14875 (2017).
7. Ando, J., Asanuma, M., Dodo, K., Yamakoshi, H., Kawata, S., Fujita, K., and Sodeoka, M.:
"Alkyne-Tag SERS Screening and Identification of Small-Molecule-Binding Sites in Protein"
J. Am. Chem. Soc. 138, 13901-13910 (2016).
8. Ando, J., Kinoshita, M., Cui, J., Yamakoshi, H., Dodo, K., Fujita, K., Murata, M., and Sodeoka, M.:
"Sphingomyelin distribution in lipid rafts of artificial monolayer membranes visualized by Raman microscopy"
Proc. Nat. Acad. Sci. 112, 4546-4551 (2015).
9. Yamaguchi, T., Asanuma, M., Nakanishi, S., Saito, Y., Okazaki, M., Dodo, K., and Sodeoka, M.:
"Turn-ON Fluorescent Affinity Labeling Using a Small Bifunctional O-Nitrobenzoxadiazole Unit"
Chem. Sci. 5, 1021-1029 (2014).
10. Yamakoshi, H., Dodo, K., Palonpon, A., Ando, J., Fujita, K., Kawata, S., and Sodeoka, M.:
"Alkyne-tag Raman Imaging for Visualization of Mobile Small Molecules in Live Cells"
J. Am. Chem. Soc. 134, 20681-20689 (2012).