| アイテムタイプ |
itemtype_ver1(1) |
| 公開日 |
2024-10-18 |
| タイトル |
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タイトル |
Effect of Brønsted Acids on the Activation of Mixed Anhydride/Mixed Carbonic Anhydride and C‐Terminal‐Free N‐Methylated Peptide Synthesis in a Micro‐Flow Reactor |
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言語 |
en |
| 著者 |
Chen, Ting‐Ho
Ando, Akira
Shamoto, Otoka
Fuse, Shinichiro
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| アクセス権 |
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アクセス権 |
open access |
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アクセス権URI |
http://purl.org/coar/access_right/c_abf2 |
| 権利 |
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権利情報 |
"This is the peer reviewed version of the following article: [T.-H. Chen, A. Ando, O. Shamoto, S. Fuse, Chem. Eur. J. 2024, 30, e202401402. https://doi.org/10.1002/chem.202401402], which has been published in final form at [https://doi.org/10.1002/chem.202401402]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited." |
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言語 |
en |
| 内容記述 |
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内容記述タイプ |
Abstract |
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内容記述 |
Amidations employing mixed (carbonic) anhydrides have long been favoured in peptide synthesis because of their cost-effectiveness and less waste generation. Despite their long history, no study has compared the effects of additives on the activation of mixed anhydrides and carbonic anhydrides. In this study, we investigated the amidation of mixed (carbonic) anhydride in the presence of a base and/or Brønsted acids. The use of NMI⋅HCl significantly improved the conversion of the mixed carbonic anhydride, while expediting nucleophilic attacks on the desired carbonyl group. In contrast, in the case of mixed anhydrides, neither the conversion nor the desired nucleophilic attack improved significantly. We developed a C-terminus-free N-methylated peptide synthesis method using mixed carbonic anhydrides in a micro-flow reactor. Fourteen N-alkylated peptides were synthesized in moderate to high yields (55–99 %) without severe racemization (<1 %). Additionally, a significant enhancement in the amidation between mixed carbonic anhydrides and bis-TMS-protected N-methyl amino acids with the inclusion of NMI⋅HCl was observed for the first time. In addition, we observed unexpected C-terminal epimerization of the C-terminus-free N-methyl peptides. |
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言語 |
en |
| 出版者 |
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出版者 |
Wiley |
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言語 |
en |
| 言語 |
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言語 |
eng |
| 資源タイプ |
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資源タイプresource |
http://purl.org/coar/resource_type/c_6501 |
|
タイプ |
journal article |
| 出版タイプ |
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出版タイプ |
AM |
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出版タイプResource |
http://purl.org/coar/version/c_ab4af688f83e57aa |
| 関連情報 |
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関連タイプ |
isVersionOf |
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識別子タイプ |
DOI |
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関連識別子 |
https://doi.org/10.1002/chem.202401402 |
| 収録物識別子 |
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収録物識別子タイプ |
PISSN |
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収録物識別子 |
0947-6539 |
| 書誌情報 |
en : Chemistry – A European Journal
巻 30,
号 38,
p. e202401402,
発行日 2024-07-05
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| ファイル公開日 |
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日付 |
2025-07-05 |
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日付タイプ |
Available |
manuscript_Chem_Eur_J.pdf (1.3 MB)
