SYNTHESIS OF A HYDROPHOBIC POTASSIUM BINDING PEPTIDE
SYNTHESIS OF A HYDROPHOBIC POTASSIUM BINDING PEPTIDE
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DOI：
10.1021/ja00772a039
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发表时间：
1972-01-01
影响因子：
15
通讯作者：
MERRIFIELD, RB
中科院分区：
文献类型：
--
作者：
GISIN, BF;MERRIFIELD, RB
基于碱离子络合剂的已知结构，进行了能够结合钾离子的同型环肽的设计。肽cvc/o-[-L-Val-D-Pro-D-Val-L-Pro-] 3的分子模型表现出这种性质，这是通过它在其最可能的构象之一中提供的氧衬空腔来判断的。以C端的L-脯氨酸为起始原料，通过固相法合成了线性肽。中性环十二肽与苦味酸钾形成1：1的疏水性结晶络合物，在金属离子配体中，所谓的“离子轴载体”是一类能与碱金属离子络合并使它们溶于非极性介质的化合物。这种品质引起了人们的极大兴趣，主要有三个原因。首先，一些离子载体显示出抗菌活性2 - 9，并且它们对线粒体1011和红细胞中的离子平衡显示出显著的影响。12· 13其次，已发现它们在脂质膜（脂质双层）和其他细胞中产生类似的作用。
Based on the known structures of alkali ion complexing agents the design of a homodetic cyclopeptide that would be able to bind the potassium ion was undertaken. A molecular model of the peptide cvc/o-[-L-Val-D-Pro-D-Val-L-Pro-] 3 exhibited that property as judged by the oxygen-lined cavity it could provide in one of its most probable conformations. The linear peptide was synthesized by the solid-phase methodstarting with L-proline at the C terminus. After cleavage from the resin and cyclization the neutral cyclododecapeptide was found to form a crystalline, hydrophobic 1: 1 complex with potassium picrate.Among the ligands for metal ions the so-called “ion ax carriers” constitute a group of compounds which are able to complex with alkali ions and make them soluble in nonpolar media. This quality has generated great interest mainly for three reasons. First, some of the ion carriers exhibit antibiotic activity2-9and they show dramatic effects on the ionic balance in mito-chondria1011 andin red blood cells. 12· 13 Second, they have been found to produce similar effects in lipid membranes18· 14 (lipid bilayers) and in other