Synthesis of cyclic peptides via O-N-acyl migration
Synthesis of cyclic peptides via O-N-acyl migration
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DOI：
10.1016/j.tetlet.2008.05.049
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发表时间：
2008-07-28
影响因子：
1.8
通讯作者：
Amblard, Muriel
中科院分区：
文献类型：
--
作者：
Lecaillon, Jennifer;Gilles, Pierre;Amblard, Muriel
本文描述了一种新颖、简便的避免消旋化的首尾相连的环肽的合成方法。在2-氯三苯甲基氯树脂上合成了含有丝氨酸残基的线性缩肽。从树脂上裂解后，在溶液中通过氨基甲酸酯保护的O-酰基丝氨酸残基的C-末端活化进行分子内首尾环化。去除N-α-丝氨酸保护基后，最后一步是在“开关”或“点击”元件上进行O-N-酰基迁移反应，以恢复天然环肽。(C)2008爱思唯尔有限公司保留所有权利。
We describe here a novel and convenient synthesis of head-to-tail cyclic peptide avoiding racemization. Linear depsipeptides including a serine residue as the key element for ester bond formation and acyl transfer were synthesized on 2-chlorotrityl chloride resin. After cleavage from the resin, intramolecular head-to-tail cyclization was performed in solution by C-terminal activation of urethane protected O-acyl serine residue. After removal of the N-alpha-serine protecting group, the final step consisted in O-N-acyl migration reaction on the 'switch' or 'click' element to restore native cyclic peptides. (C) 2008 Elsevier Ltd. All rights reserved.