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2019 Fiscal Year Final Research Report

Development of chemical reactions for realizing precise synthesis of low to high molecular weight bioactive compounds in aqueous solutions

Research Project

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Project/Area Number 16K17902
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionInstitute of Physical and Chemical Research (2018-2019)
Kyushu University (2016-2017)

Principal Investigator

Watanabe Kenji  国立研究開発法人理化学研究所, 生命機能科学研究センター, 研究員 (90631937)

Project Period (FY) 2016-04-01 – 2020-03-31
Keywords水中反応 / チオール / タンパク質 / ペプチド / インドール
Outline of Final Research Achievements

In this study, we developed chemical reactions and related transformations for precise chemical modification of biomolecules such as proteins, peptides, and amino acids. We reported alcohol compounds having an indole skeleton selectively form a stable C-S bond with a thiol group via dehydroxylation of the hydroxy group in a weakly acidic (pH 4.5-6.4) aqueous buffered solutions (Chem. Eur. J. 2018, 24, 3959-3964). We also investigated a related transformation involving thiol and boronic acid that proceeds in organic solvents. In the final year, we conducted a comparative study between the latest bioconjugation reactions and covalent bond formation reactions involving thiols, and published a review (J. Synth. Org. Chem. Jpn. 2019, 77, 841-842).

Free Research Field

生体機能関連化学

Academic Significance and Societal Importance of the Research Achievements

タンパク質などの生体由来の分子と生物活性を示す有機化合物を結びつける化学反応についての研究を行った。これまでに用いられてきた化学反応は、タンパク質のチオール基の空気酸化や反応性の高いアミノ基が関与する望まない副反応が起こり、問題となることがあったが、これらを克服した弱酸性条件で進行する新たな化学反応の開発を行った。これらの成果は、医薬品や生命機能を解明するための分子を合成するために役立つと考えられる。

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Published: 2021-02-19  

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