Chirayil Sara, Luebke Kevin J
Division of Cardiology, Department of Internal Medicine, University of Texas Southwestern Medical Center, 5323 Harry Hines Blvd., Dallas, Texas, 75390-8573 USA.
Tetrahedron Lett. 2012 Feb 15;53(7):726-729. doi: 10.1016/j.tetlet.2011.12.002. Epub 2011 Dec 8.
Introduction of conformational constraints into peptoids (N-substituted oligoglycines) will enable new applications in molecular recognition and self-assembly. Peptoids that contain both a phenylboronic acid side chain and a 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 to 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.
将构象限制引入类肽(N-取代寡甘氨酸)将在分子识别和自组装方面带来新的应用。同时含有苯硼酸侧链和邻二醇的类肽通过分子内缩合环化形成硼酸酯。使用游离硼酸的荧光指示剂来测定酯化反应。在类肽中,距离硼酸侧链2至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,80-90%的类肽发生环化。当二醇是简单的2,3-二羟丙基时,酯化反应不太有利,但仍然可观。