2018 Fiscal Year Final Research Report
Breakthrough design of unusual transition states in stereoselective glycosylations
| Project/Area Number |
16KT0061
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Multi-year Fund |
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| Section | 特設分野 |
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| Research Field |
Transition State Control
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| Research Institution | Toho University |
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Principal Investigator |
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| Co-Investigator(Kenkyū-buntansha) |
山田 英俊 関西学院大学, 理工学部, 教授 (90200732)
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| Project Period (FY) |
2016-07-19 – 2019-03-31
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| Keywords | グリコシル化反応 / 立体制御 / α-グルコシド / β-マンノシド / 3,6-架橋糖 / 2,6-ラクトン |
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| Outline of Final Research Achievements |
We have designed and made use of two classes of glycosyl donors with unusual conformations. 2,6-Lactones are rigidly fixed to a boat-like conformation and offer 1,2-cis-β-stereoselective glycosylations through stereoinvertive mechanisms, whereas 3,6-loosely-bridged glucoses are supple and offer 1,2-cis-α-stereoselective glycosylations via the corresponding glycosyl cations. The latter allowed us to synthesize record-small cyclodextrins, which are composed of three or four sugar residues.
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| Free Research Field |
糖質合成化学
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| Academic Significance and Societal Importance of the Research Achievements |
生体反応では，糖の多様な立体配座を巧みに駆使し，高効率な反応を実現しているのに対し，化学的グリコシル化反応では，38の（準）安定配座のうち，極めて限られた配座のみが用いられてきた．一方，本研究では，従来活用されてこなかった配座に固定された糖（配座固定糖）や，従来よりも容易に配座を転換できる糖（配座柔軟化糖）をデザイン・合成し，それらが，糖質の精密合成において威力を発揮することを示した．
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