Preparation of Organosoluble Silica-Polypeptide Particles by "Click" Chemistry
Preparation of Organosoluble Silica-Polypeptide Particles by "Click" Chemistry
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DOI：
10.1021/ma901840n
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发表时间：
2010-01-12
期刊：
影响因子：
5.5
通讯作者：
Russo, Paul S.
中科院分区：
文献类型：
--
作者：
Balamurugan, Sreelatha S.;Soto-Cantu, Erick;Russo, Paul S.
通过开环聚合和点击化学相结合的方法，合成了具有疏水、α-螺旋多肽壳和二氧化硅核的有机可溶杂化粒子。以丙叉胺为引发剂，通过N-硬脂酰基-α-L-谷氨酸酯的N-羧酸酐开环聚合，制备了α-L-谷氨酸-α-硬脂酰-N-羧酸乙酯的开环聚合产物。用凝胶渗透色谱(GPC)和差示扫描量热法(MALDI)表征了多肽的相对分子质量和结构，用核磁共振氢谱(H-1NMR)和傅立叶变换红外光谱(FTIR)确定了该多肽的α-螺旋性质。用3-溴丙基三氯硅烷对二氧化硅颗粒进行官能化，然后用叠氮化钠进行亲核取代，制得叠氮功能化二氧化硅颗粒(叠氮二氧化硅)。通过FTIR MID XPS对叠氮化产物进行了表征。在五甲基二乙三胺和溴化铜(L)存在下，在四氢呋喃或甲苯中，炔-PSLG通过点击反应偶联到叠氮硅胶上。用XPS、FTIR和H-1核磁共振对产物进行了进一步的表征，结果表明接枝的多肽保持了α-螺旋的性质，并形成了易于分散在有机溶剂中的胶体颗粒。这些疏水的多肽功能化粒子可以作为胶体动力学和/或结晶研究的模型系统。它们也可能用于模拟酶的激活或细胞膜中疏水蛋白质的性质的研究。
The synthesis of organo-soluble hybrid particles With a hydrophobic, alpha-helical polypeptide shell and silica core has been achieved by combining ring-opening polymerization and click chemistry. Alkyne end-terminated poly(gamma-stearyl-alpha-L-glutamate) (alkyne-PSLG) was prepared by the ring-opening polymerization of the N-carboxyanhydride of gamma-stearyl-alpha-L-glutamate using propargylamine Lis initiator. The molecular weight and structure of this polypeptide were characterized by GPC and MALDI, and the alpha-helical nature was established by H-1 NMR and FTIR. Azide-functionalized silica particles (azido-silica) were prepared by the functionalization of silica particles with 3-bromopropyltrichlorosilane followed by nucleophilic substitution with sodium azide. The azide functionalization was confirmed by FTIR mid XPS. Alkyne-PSLG was coupled to azido-silica by click reaction in tetrahydrofuran or toluene in the presence of pentamethyldiethylene-triamine and copper(l) bromide. Further characterization of the product using XPS, FTIR, and H-1 NMR revealed that the grafted polypeptide retained its alpha-helical nature and formed colloidal particles that readily dispersed in organic solvents. These hydrophobic, polypeptide-functionalized particles can serve as model systems in studies of colloid dynamics and/or crystallization. They may also find use in investigations designed to model enzyme activation or the properties of hydrophobic proteins in cell membranes.