Small gold nanoparticles for interfacial Staudinger-Bertozzi ligation
Small gold nanoparticles for interfacial Staudinger-Bertozzi ligation
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DOI：
10.1039/c5ob00372e
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发表时间：
2015-01-01
影响因子：
3.2
通讯作者：
Workentin, Mark S.
中科院分区：
文献类型：
--
作者：
Gobbo, Pierangelo;Luo, Wilson;Workentin, Mark S.
成功地合成了具有甲基-2-（二苯基膦）苯甲酸酯部分界面的小金纳米颗粒（Staudinger-AuNPs），并通过多核磁共振光谱、透射电子显微镜（TEM）、紫外-可见光谱、热重分析和x射线光电子能谱（XPS）对其进行了表征。特别是，XPS对表征新型纳米材料非常敏感，并提供了其界面反应性的证据。发现这些staudinger - aunp对磷化氢中心的氧化是稳定的。以Staudinger-Bertozzi连接反应为模型体系，采用P-31核磁共振波谱法研究了叠氮苄基反应。表明界面反应干净、定量。为了展示这些Staudinger-AuNPs在生物有机化学中的潜在用途，通过Staudinger-AuNPs与一种新型叠氮标记的CRGDK肽反应制备了AuNP生物偶联物。CRGDK肽可以高效、化学选择性和高负载地与AuNP共价结合。
Small gold nanoparticles (AuNPs) that possess interfacial methyl-2-(diphenylphosphino)benzoate moieties have been successfully synthesized (Staudinger-AuNPs) and characterized by multi-nuclear MR spectroscopy, transmission electron microscopy (TEM), UV-Vis spectroscopy, thermogravimetric analysis, and X-ray photoelectron spectroscopy (XPS). In particular, XPS was remarkably sensitive for characterization of the novel nanomaterial, and in furnishing proof of its interfacial reactivity. These Staudinger-AuNPs were found to be stable to the oxidation of the phosphine center. The reaction with benzyl azide in a Staudinger-Bertozzi ligation, as a model system, was investigated using P-31 NMR spectroscopy. This demonstrated that the interfacial reaction was clean and quantitative. To showcase the potential utility of these Staudinger-AuNPs in bioorganic chemistry, a AuNP bioconjugate was prepared by reacting the Staudinger-AuNPs with a novel azide-labeled CRGDK peptide. The CRGDK peptide could be covalently attached to the AuNP efficiently, chemoselectively, and with a high loading.