Interior surface modification of bacteriophage MS2
Interior surface modification of bacteriophage MS2
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DOI：
10.1021/ja031790q
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发表时间：
2004-03-31
影响因子：
15
通讯作者：
Francis, MB
中科院分区：
文献类型：
--
作者：
Hooker, JM;Kovacs, EW;Francis, MB
报道了一种有效的MS 2病毒衣壳内表面功能化策略，其特征在于新的异源Diels −桤木生物缀合反应。病毒分离后，通过暴露于pH 11.8条件4小时，从球形颗粒中除去RNA基因组。在此之后，通过使用位点选择性重氮偶联反应来修饰每个“空”衣壳壳的内表面上的180个酪氨酸残基。为了连接额外的功能，偶氮缀合物用Na 2S 2 O 4还原，得到邻氨基酪氨酸衍生物。用NaIO 4氧化该部分，在蛋白质表面上产生氨基亚氨基醌，发现其与N-（4-氨基苯基）丙烯酰胺进行有效的异Diels −桤木反应。该四步程序可以在4小时内进行，达到高水平的转化率，并以>60%的总产率产生所需的缀合物。
An efficient strategy for the interior surface functionalization of MS2 viral capsids is reported, featuring a new hetero-Diels−Alder bioconjugation reaction. After virus isolation, the RNA genome was removed from the spherical particles by exposure to pH 11.8 conditions for a period of 4 h. Following this, 180 tyrosine residues on the interior surface of each “empty” capsid shell were modified by using a site-selective diazonium-coupling reaction. To attach additional functionality, the azo conjugate was reduced with Na2S2O4to afford an ortho-amino tyrosine derivative. Oxidation of this moiety with NaIO4produced ano-iminoquinone on the protein surface, which was found to undergo an efficient hetero-Diels−Alder reaction withN-(4-aminophenyl)acrylamide. This four-step procedure can be carried out in under 4 h, reaches high levels of conversion, and yields the desired conjugates in >60% overall yield.