Development of a novel glycosylation reaction between unprotected carbohydrates for rapid polysaccharide synthesis

2023 Fiscal Year Final Research Report

• Project/Area Number: 21K14636
• Research Category: Grant-in-Aid for Early-Career Scientists
• Allocation Type: Multi-year Fund
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: Institute of Physical and Chemical Research
• Principal Investigator: Kusano Shuhei 国立研究開発法人理化学研究所, 環境資源科学研究センター, 研究員 (80759291)
• Project Period (FY): 2021-04-01 – 2024-03-31
• Keywords: グリコシル化 / 糖鎖 / 保護基 / 有機ホウ素触媒

Outline of Final Research Achievements

Glycosylation reaction typically requires protecting groups to control the regioselectivity and stereoselectivity. However, this synthetic strategy depending on protecting groups has an inherent drawback: tedious protection-deprotection sequences result in lengthy and inefficient synthetic processes. In this study, we developed the bifunctional benzoxaborole serving as a catalyst of glycosylation reaction without using protecting groups. We established the new concept of catalyst design and the new strategy of glycosylation reactions.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

構造の均一性が担保された化学合成糖鎖は，糖鎖研究を進める上で不可欠な研究試料である．本研究では，糖鎖合成を短工程化しうる無保護糖のグリコシル化反応の開発に取り組み，反応の位置選択性と立体選択性を制御するための新たな知見を見出すことに成功した．加えて，本研究を通じて確立した触媒設計戦略は，有機ホウ素触媒に共通するものであり，触媒技術体系の一層の発展に貢献するものと期待される．