Asymmetric construction of arylglycine unit and application to the synthesis of unnatural amino acid-containing peptide
| Project/Area Number |
18K14869
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| Research Category |
Grant-in-Aid for Early-Career Scientists
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| Allocation Type | Multi-year Fund |
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| Review Section |
Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
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| Research Institution | The University of Tokushima |
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Principal Investigator |
INOKUMA Tsubasa 徳島大学, 大学院医歯薬学研究部(薬学域), 助教 (40541272)
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| Project Period (FY) |
2018-04-01 – 2020-03-31
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| Project Status |
Completed (Fiscal Year 2019)
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| Budget Amount *help |
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | ペプチド合成 / アリールグリシン / 不斉触媒 / アリール化 / イミン / 異常アミノ酸 / ペプチド / 不斉合成 / 非天然アミノ酸 |
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| Outline of Final Research Achievements |
We previously developed a methodology for synthesis of non-canonical amino acid-containing peptide via direct asymmetric reaction to peptidic substrate. In this study, we planned to develop an asymmetric arylation to imino peptide for synthesis of peptide containing aryalglycine which is one of the non-canonical amino acid. As a result, although the substrate scope is somewhat narrow, we succeeded in developing an asymmetric arylation to model substrates in good yields and stereoselectivities.
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| Academic Significance and Societal Importance of the Research Achievements |
ペプチドはそのアミノ酸配列に応じて多様な機能を付与できることから近年新たな医薬品候補化合物として注目されており、その構成成分を異常アミノ酸まで拡張すれば構造多様性が大きく拡充され新規医薬品創出の可能性が飛躍的に向上する。代表者が考案したペプチドへの直接的不斉反応は、不斉反応時の求核剤を変更するのみで多様な側鎖構造の異常アミノ酸をペプチド鎖に迅速に導入できる。そのため、本合成プロセスの反応適用拡大は異常アミノ酸含有ペプチドを基盤とする創薬研究を推し進める大きな駆動力となる。
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Report
(3 results)
Research Products
(14 results)
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[Journal Article] Development of a 1,3a,6a-Triazapentalene Derivative as a Compact and Thiol-specific Fluorescent Labeling Reagent2020
Author(s)
Atsushi Nakayama, Akira Otani, Tsubasa Inokuma, Daisuke Tsuji, Haruka Mukaiyama, Akira Nakayama, Kohji Itoh, Akira Otaka, Keiji Tanino, and Kosuke Namba
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Journal Title
Communications Chemistry
Volume: 3
Issue: 1
Pages: 1-9
DOI
NAID
Related Report
Peer Reviewed / Open Access
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