2-氯三苯甲基氯树脂。Fmoc-氨基酸的锚定及肽裂解研究。

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

作者信息

Barlos K, Chatzi O, Gatos D, Stavropoulos G

机构信息

Department of Chemistry, University of Patras, Greece.

出版信息

Int J Pept Protein Res. 1991 Jun;37(6):513-20.

PMID:1917309

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.

摘要

研究了在二异丙基乙胺（DIEA）存在下，2-氯三苯甲基氯树脂与Fmoc-氨基酸的酯化反应在各种条件下的情况。在二氯甲烷（DCM）或1,2-二氯乙烷（DCE）中，使用0.6当量的Fmoc-氨基酸/毫摩尔树脂，在室温下25分钟内可获得较高的酯化产率。即使对于Fmoc-天冬酰胺（Fmoc-Asn）和Fmoc-谷氨酰胺（Fmoc-Gln），反应也不会生成副产物。通过使用乙酸（AcOH）/2,2,2-三氟乙醇（TFE）/DCM混合物，在室温下15 - 60分钟内即可实现从2-氯三苯甲基树脂上定量且轻松地裂解氨基酸和肽，而叔丁基型保护基团不受影响。在这些异常温和的条件下，从树脂上裂解氨基酸和肽时产生的2-氯三苯甲基阳离子不会攻击色氨酸（Trp）、甲硫氨酸（Met）和酪氨酸（Tyr）的亲核侧链。