Selective Chemical Trasformation of Specific Sugars for Diversification of Glycan Mediating Membrane Dynamics

2023 Fiscal Year Final Research Report

• Project Area: Regulation of membrane dynamics by glycan chemical knock-in
• Project/Area Number: 21H05078
• Research Category: Grant-in-Aid for Transformative Research Areas (B)
• Allocation Type: Single-year Grants
• Review Section: Transformative Research Areas, Section (II)
• Research Institution: National Institute of Advanced Industrial Science and Technology (2022-2023); Kyoto University (2021)
• Principal Investigator: Ueda Yoshihiro 国立研究開発法人産業技術総合研究所, 材料・化学領域, 主任研究員 (90751959)
• Project Period (FY): 2021-08-23 – 2024-03-31
• Keywords: 糖 / 化学変換 / 位置選択性 / 機能制御 / アシル化 / シリル化

Outline of Final Research Achievements

Precise synthesis of well-defined sugar derivatives is necessary to understand and control biological phenomena involving carbohydrates. In this study, we worked on the development of a method for selective chemical modification of a particular site on sugars. During the course of the study, a method for catalytic selective acylation of glucose derivatives was developed. In addition to acylation, we have discovered site-selective silylation of glucose derivatives and substrate-selective silylation of amino alcohols. By applying the developed selective functional group transformation method to the caging of bioactive sugars, we were able to develop a method to control sugar functions on the cell surface through collaborative research.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

糖はアミノ酸と並び生体高分子の主要な構成成分であり、広範な生体内反応に関わっている。糖が関与する生命現象を理解し制御するためには、化学的に純粋な糖関連物質の精密合成が必要となるが、糖は分子内に複数の水酸基を有するため、合成や修飾には煩雑な保護/脱保護工程が必要であった。本研究では保護基を利用しない方法論の発展を目指し数種の新規選択的反応開発を行うことができた。独自の選択的反応をツールとして活用することで新しい生命科学研究にも展開することができ、合成化学から生命科学に波及効果をもたらす成果を挙げることができた。