Water-Soluble Chiral Metallopeptoids
Water-Soluble Chiral Metallopeptoids
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DOI：
10.1002/bip.22675
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发表时间：
2015-09-01
期刊：
影响因子：
2.9
通讯作者：
Maayan, Galia
中科院分区：
文献类型：
--
作者：
Baskin, Maria;Maayan, Galia
金属离子在生物系统的活性中发挥着重要作用，包括催化、识别和折叠。因此，将金属离子引入到拟肽低聚物中是创建仿生金属配合物的一种潜在方法，可用于传感、识别、药物设计和催化。在此，我们报告了水溶性手性N-取代甘氨酸寡聚物“类肽”的设计、合成和表征，该寡聚物具有一个和两个不同的分子内金属离子（例如铜和钴）结合位点。我们首次证明了在类肽序列中掺入了手性亲水基团 (S)-(1)-1-甲氧基-2-丙胺 (Nsmp)，从而提供了手性和水溶性。使用亚单体方法在固体支持物上合成了两个类肽、一个七聚体和一个十二聚体，分别带有两个和四个 8-羟基喹啉 (HQ) 基团作为金属结合配体。使用 UV 滴定和 ESI-MS 分析，我们证明了通过分子内螯合在不同结合位点带有两个金属离子的新型金属肽的创建。激子对圆二色性（ECCD）证明了从手性非螺旋类肽到金属中心的手性感应。 (C) 2015 年 Wiley 期刊公司。
Metal ions play a significant role in the activity of biological systems including catalysis, recognition and folding. Therefore, introducing metal ions into peptidomimetic oligomers is a potential way for creating biomimetic metal complexes toward applications in sensing, recognition, drug design and catalysis. Herein we report the design, synthesis and characterization of water-soluble chiral N-substituted glycine oligomers, "peptoids," with one and two distinct intramolecular binding sites for metal ions such as copper and cobalt. We demonstrate for the first time the incorporation of the chiral hydrophilic group (S)-(1)-1-methoxy-2-propylamine (Nsmp) within peptoid sequences, which provides both chirality and water solubility. Two peptoids, a heptamer, and a dodecamer bearing two and four 8-hydroxyquinoline (HQ) groups respectively as metal-binding ligands, were synthesized on solid support using the submonomer approach. Using UV-titrations and ESI-MS analysis we demonstrate the creation of a novel metallopeptoid bearing two metal ions in distinct binding sites via intramolecular chelation. Exciton couplet circular dichroism (ECCD) demonstrated chiral induction from the chiral non-helical peptoids to the metal centers. (C) 2015 Wiley Periodicals, Inc.