Photo-induced site-selective deoxigenation and functionalization of sugars

2020 Fiscal Year Final Research Report

• Project/Area Number: 19K15562
• 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: Kyoto University
• Principal Investigator: Masuda Yusuke 京都大学, 工学研究科, 特定助教 (20822307)
• Project Period (FY): 2019-04-01 – 2021-03-31
• Keywords: 糖 / 水 / 光

Outline of Final Research Achievements

Sugars play an essential role in biological functions, and it is highly desired to develop the methods for efficiently transforming these natural compounds in synthetic organic chemistry. In this study, we developed the direct conversion of unprotected sugars by photo-irradiation in water: Unprotected aldoses such as glucose and ribose were directly transformed to 2-deoxysugars under photo-irradiation by using water-soluble ketone as a catalyst. Furthermore, a water-soluble iridium photocatalyst found to be more efficient for photo-isomerization of sugars, and a wide range of sugars could be converted to the corresponding 2-deoxysugars under mild reaction conditions. Deoxysugars are an important class of natural compounds found in DNA and erythromycin, and they can be directly synthesized from readily available unprotected sugars by the present method.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究は、水中での光反応が糖類の変換に効果的であることを示した点で学術的意義が大きい。従来の有機溶媒中での反応では、糖類を適切に修飾することでその溶解性や反応性を制御していた。しかし、修飾過程における行程数や廃棄物の増加が問題であった。一方本研究では光を用いることで、有機溶媒の使用と反応前修飾の二つの問題を解決し、高効率かつ高付加価値な糖類変換反応を達成した。本手法は既存の糖類の合成を効率化するだけでなく、新規糖類縁体の合成に役立つことから、医薬や材料など幅広い分野への波及効果が期待できる。