Surface modification of tobacco mosaic virus with "Click" chemistry
Surface modification of tobacco mosaic virus with "Click" chemistry
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DOI：
10.1002/cbic.200700559
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发表时间：
2008-03-03
期刊：
影响因子：
3.2
通讯作者：
Wang, Qian
中科院分区：
文献类型：
--
作者：
Bruckman, Michael A.;Kaur, Gagandeep;Wang, Qian
CuI催化的叠氮-炔1，3-偶极环加成（CuAAC）反应[1，2]是著名的Huisgen反应的复兴[3]，近年来在有机合成、药物发现、高分子和材料科学以及生物技术中得到了广泛的应用。[4-7]高的反应产率、简单的反应和纯化条件、宽范围的溶剂和pH稳定性以及官能团耐受性使得CuAAC反应成为典型的“点击化学”，[8]是将功能结合到所需支架上的理想选择。多年来，它已被广泛用于构建和官能化聚合物和多价展示系统，包括聚合物、[9-16]树枝状聚合物、[17，18]纳米颗粒[19]和表面[20-22]，其中期望每个单元反应的极高反应效率。[23特别地，由于有机叠氮化物和炔几乎不与生物分子和水反应，CuAAC反应已用于在温和的反应条件下高效地衍生生物大分子、[25，26]病毒[27-29]和细胞[30-32]。近年来，酪氨酸残基被认为是一个特别有吸引力的目标，化学选择性修饰的蛋白质，因为它的亚丰度分布。弗朗西斯和同事们已经报道了许多转化，从曼尼希型反应到过渡金属介导的烯丙基化反应再到重氮偶联反应，其可以在生理条件下有效地靶向酪氨酸残基的酚基。[33-36]为了克服与富含电子的重氮盐的缓慢反应性，开发了顺序还原/氧化/Diels-Alder反应以打破引入的官能团的限制。[36]在这篇文章中，我们报告说，CuAAC反应可以与重氮偶联反应相结合，以多种起始材料定量功能化酪氨酸残基。烟草花叶病毒（TMV）是棒状植物病毒的典型例子，由2130个相同的蛋白质亚基组成围绕基因组单个RNA链螺旋排列。TMV的长度，即300 nm，由稳定外壳蛋白组装的封装的基因组RNA限定。TMV的极性外表面和内表面已被用作生长金属或金属氧化物纳米线的模板[36-43]，并且导电聚合物已被涂覆在1D组装的TMV上，
CuI-catalyzed azide-alkyne 1, 3-dipolar cycloaddition (CuAAC) reaction,[1, 2] renascent of the well-known Huisgen reaction,[3] has recently flourished with applications in organic synthesis, drug discovery, polymer and materials science, and biotechnology.[4–7] The high reaction yield, simple reaction and purification conditions, wide range of solvent and pH stabilities, and functional group tolerance make the CuAAC reaction a prototypical “click chemistry”,[8] ideal for incorporating functionalities onto desired scaffolds. Over the years it has been widely employed to construct and functionalize polymeric and polyvalent display systems, including polymers,[9–16] dendrimers,[17, 18] nanoparticles,[19] and surfaces,[20–22] where an extremely high reaction efficiency for every unit reaction is desirable.[23, 24] In particular, as organic azides and alkynes are almost unreactive with biomolecules and water, CuAAC reactions have been employed in derivatizing biomacromolecules,[25, 26] viruses,[27–29] and cells [30–32] with high efficacy under mild reaction conditions. Recently tyrosine residues have been considered as a particularly attractive target for chemoselective modification of proteins because of its subabundant distribution. Francis and coworkers have reported a number of transformations, ranging from the Mannich-type reaction to a transition metal mediated allylation reaction to a diazonium-coupling reaction, which can efficiently target the phenolic group of tyrosine residues at physiological conditions.[33–36] To overcome the sluggish reactivity with electron-enriched diazonium salts, a sequential reduction/oxidation/Diels–Alder reaction was developed to break the limitation of functionalities being incorporated.[36] In this communication, we report that CuAAC reactions can be combined with a diazonium-coupling reaction to quantitatively functionalize tyrosine residues with a wide array of starting materials.Tobacco Mosaic Virus (TMV) is a classic example of rodlike plant viruses consisting of 2130 identical protein subunits arranged helically around genomic single RNA strand. The length of TMV, that is, 300 nm, is defined by the encapsulated genomic RNA that stabilizes the coat protein assembly. The polar outer and inner surfaces of TMV have been exploited as templates to grow metal or metal oxide nanowires,[36–43] and conductive polymers have been coated on 1D assembled TMV to