2-Chlorotrityl chloride resin. Studies on anchoring of Fmoc-amino acids and peptide cleavage.

K Barlos, O Chatzi, D Gatos, G Stavropoulos
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引用次数: 0

Abstract

The esterification of 2-chlorotrityl chloride resin with Fmoc-amino acids in the presence of DIEA is studied under various conditions. High esterification yields are obtained using 0.6 equiv. Fmoc-amino acid/mmol resin in DCM or DCE, in 25 min, at room temperature. The reaction proceeds without by product formation even in the case of Fmoc-Asn and Fmoc-Gln. The quantitative and easy cleavage of amino acids and peptides from 2-chlorotrityl resin, by using AcOH/TFE/DCM mixtures, is accomplished within 15-60 min at room temperature, while t-butyl type protecting groups remain unaffected. Under these exceptionally mild conditions 2-chlorotrityl cations generated during the cleavage of amino acids and peptides from resin do not attack the nucleophilic side chains of Trp, Met, and Tyr.

2-氯三烷基氯树脂。fmoc氨基酸的锚定与肽切割的研究。
研究了在DIEA存在下2-氯三酰氯树脂与fmoc氨基酸在不同条件下的酯化反应。在室温下,在DCM或DCE中使用0.6等量的fmoc -氨基酸/mmol树脂,在25分钟内获得了较高的酯化率。即使在Fmoc-Asn和Fmoc-Gln的情况下,反应也没有产生副产物。在室温下,AcOH/TFE/DCM混合物可以在15-60分钟内完成2-氯三烷基树脂中氨基酸和肽的定量和容易切割,而t-丁基型保护基团不受影响。在这些异常温和的条件下,氨基酸和多肽从树脂中裂解时产生的2-氯三甲基阳离子不会攻击Trp、Met和Tyr的亲核侧链。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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