| Project/Area Number |
16K18847
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Chemical pharmacy
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| Research Institution | Nagasaki University |
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Principal Investigator |
UEDA Atsushi 長崎大学, 医歯薬学総合研究科(薬学系), 助教 (10732315)
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Project Status |
Completed (Fiscal Year 2018)
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| Budget Amount *help |
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2017: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
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| Keywords | アミノ酸 / ペプチド / 二次構造 / ジ置換アミノ酸 / 有機分子触媒 / 薬学 / 有機化学 |
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| Outline of Final Research Achievements |
Stapled peptide possessing carbocyclic α, α-disubstituted α-amino acids was synthesized by standard solution-phase synthesis followed by ring-closing metathesis reaction. Conformational freedom-restricted peptides were used as an asymmetric organocatalyst for Michael addition of nitroalkanes and dialkyl malonates to α, β-unsaturated ketone, and high enantioselectivities were observed with broad substrate scope. X-ray crystallographic analysis of the peptide showed α-helical structure. Stereoselective synthesis of 2,4,5-trisubstituted tetrahydropyran was also demonstrated.
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| Academic Significance and Societal Importance of the Research Achievements |
ペプチドは生体内においても重要な役割を担っており、機能性分子として働くことが知られている。このような生理活性ペプチドの多くは一定の二次構造をとることから、コンフォメーションを制御したペプチドの合成は必須となってくる。今回の成果ではコンフォメーションを制御したペプチドを不斉有機分子触媒として機能性の評価をおこなったが、今後は生理活性ペプチド等への展開も期待される。
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