2-Chlorotrityl chloride resin. Studies on anchoring of Fmoc-amino acids and peptide cleavage.
2-Chlorotrityl chloride resin. Studies on anchoring of Fmoc-amino acids and peptide cleavage.
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2-氯三酰氯树脂。
DOI：
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发表时间：
2009
期刊：
影响因子：
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通讯作者：
G. Stavropoulos
中科院分区：
文献类型：
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作者：
K. Barlos;O. Chatzi;D. Gatos;G. Stavropoulos
研究了2-氯三苯甲基氯树脂与Fmoc-氨基酸在DIEA存在下的酯化反应。使用0.6equiv. Fmoc-氨基酸/mmol树脂的DCM或DCE溶液，25 min，室温。即使在Fmoc-Asn和Fmoc-Gln的情况下，反应也在没有副产物形成的情况下进行。通过使用AcOH/TFE/DCM混合物，在室温下在15-60分钟内完成从2-氯三苯甲基树脂上定量且容易地裂解氨基酸和肽，而叔丁基型保护基团不受影响。在这些异常温和的条件下，在从树脂上裂解氨基酸和肽的过程中产生的2-氯三苯甲基阳离子不会攻击Trp、Met和Tyr的亲核侧链。
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.