Carboxylic Acid-Catalysed Transamidation of Boc-Protected Diketopiperazines (Boc-DKPs) for Peptide Synthesis

IF 2.7 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2024-12-27 DOI:10.1002/ejoc.202401319
Dr. Kazumasa Kon, Prof. Dr. Hisashi Yamamoto
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Abstract

A carboxylic acid-catalysed transamidation of Boc-protected diketopiperazines (Boc-DKPs) was developed in this study, which allowed access to various tripeptides featuring a D-proline residue in good-to-high yields within 30 min. Subsequent coupling reactions between the Boc-DKPs and di-, tri-, and tetrapeptide esters were successfully performed, furnishing the corresponding tetra-, penta-, and hexapeptides.

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羧酸催化Boc‐保护的二酮哌嗪(Boc‐DKPs)的转酰胺化用于肽合成
本研究开发了一种羧酸催化的Boc保护的二酮哌嗪(Boc‐DKPs)的转酰胺化方法,该方法可以在30分钟内以高产率获得具有D‐脯氨酸残基的各种三肽。随后,Boc‐DKPs与二、三、四肽酯之间成功地进行了偶联反应,生成了相应的四、五、六肽。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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