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Design and Synthesis of Helical N-Terminal l-Prolyl Oligopeptides Possessing Hydrocarbon Stapling
http://hdl.handle.net/10069/40371
http://hdl.handle.net/10069/40371c855ffb9-e090-418a-9fac-bf8e99c3b957
名前 / ファイル | ライセンス | アクション |
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molecules25_4667.pdf (2.4 MB)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2020-10-30 | |||||
タイトル | ||||||
タイトル | Design and Synthesis of Helical N-Terminal l-Prolyl Oligopeptides Possessing Hydrocarbon Stapling | |||||
言語 | ||||||
言語 | eng | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Helix | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Hydrocarbon stapling | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | L-proline | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Michael addition | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Organocatalyst | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Peptide | |||||
キーワード | ||||||
主題Scheme | Other | |||||
主題 | Ring-closing metathesis | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者 |
Ueda, Atsushi
× Ueda, Atsushi× Higuchi, Mei× Sato, Kazuki× Umeno, Tomohiro× Tanaka, Masakazu |
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抄録 | ||||||
内容記述タイプ | Abstract | |||||
内容記述 | We designed and synthesized helical short oligopeptides with an L-proline on the N-terminus and hydrocarbon stapling on the side chain. Side-chain stapling is a frequently used method for the development of biologically active peptides. Side-chain stapling can stabilize the secondary structures of peptides, and, therefore, stapled peptides may be applicable to peptide-based organocatalysts. Olefin-tethered cis-4-hydroxy-L-proline 1 and L-serine 2 and 8, and (R)-αallyl-proline 18 were used as cross-linking motifs and incorporated into helical peptide sequences. The Z- and E-selectivities were observed for the ring-closing metathesis reactions of peptides 3 and 11 (i,i+1 series respectively, while no E/Z-selectivity was observed for that of 19 (i,i+3 series). The stapled peptide B' catalyzed the Michael addition reaction of 1-methylindole to α,β-unsaturated aldehyde, which was seven times faster than that of unstapled peptide B. Furthermore, the high catalytic activity was retained even at lower catalyst loadings (5 mol %) and lower temperatures (0 °C). The circular dichroism spectra of stapled peptide B' showed a right-handed helix with a higher intensity than that of unstapled peptide B. These results indicate that the introduction of side-chain stapling is beneficial for enhancing the catalytic activity of short oligopeptide catalysts. |
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書誌情報 |
Molecules 巻 25, 号 20, p. 4667, 発行日 2020-10-13 |
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出版者 | ||||||
出版者 | MDPI | |||||
EISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 14203049 | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | 10.3390/molecules25204667 | |||||
権利 | ||||||
権利情報 | c2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open accessarticle distributed under the terms and conditions of the Creative Commons Attribution(CC BY) license (http://creativecommons.org/licenses/by/4.0/). | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
引用 | ||||||
内容記述タイプ | Other | |||||
内容記述 | Molecules, 25(20), art.no.4667; 2020 |