Cyclization of peptoids by formation of boronate esters
Cyclization of peptoids by formation of boronate esters
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DOI：
10.1016/j.tetlet.2011.12.002
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发表时间：
2012-02-15
影响因子：
1.8
通讯作者：
Luebke, Kevin J.
中科院分区：
文献类型：
--
作者：
Chirayil, Sara;Luebke, Kevin J.
在类肽（N-取代的寡聚甘氨酸）中引入构象约束将使其在分子识别和自组装中具有新的应用。含有苯基硼酸侧链和邻位二醇的类肽通过分子内缩合环化以形成硼酸酯。用游离硼酸荧光指示剂测定酯化反应。类肽中距离硼酸侧链2-5个单体单元的半乳糖部分与硼酸反应，与指示剂竞争。在每种情况下，分子内反应占主导地位，80-90%的类肽环化。当二醇是简单的2，3-二羟丙基时，酯化不太有利，但仍然是可感知的。(C)2011爱思唯尔有限公司保留所有权利。
Introduction of conformational constraints into peptoids (N-substituted oligoglycines) will enable new applications in molecular recognition and self-assembly. Peptoids that contain both phenylboronic acid side chain and vicinal diol cyclize by intramolecular condensation to form boronate esters. A fluorescent indicator of free boronic acid was used to assay esterification. A galactose moiety 2-5 monomer units away from a boronic acid side chain in a peptoid reacts with the boronic acid in competition with the indicator. The intramolecular reaction predominates in each case, with 80-90% of the peptoid cyclized. When the diol is a simple 2,3-dihydroxypropyl group, esterification is less favored but still appreciable. (C) 2011 Elsevier Ltd. All rights reserved.