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Bifunctional Diaminoterephthalate Fluorescent Dye as Probe for Cross-Linking Proteins

机译:双官能二苯二甲酸酯荧光染料作为交联蛋白的探针

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摘要

Diaminoterephthalates are fluorescent dyes and define scaffolds, which can be orthogonally functionalized at their two carboxylate residues with functional residues bearing task specific reactive groups. The synthesis of monofunctionalized dyes with thiol groups for surface binding, an azide for click chemistry, and a biotinoylated congener for streptavidin binding is reported. Two bifunctionalized dyes were prepared: One with an azide for click chemistry and a biotin for streptavidin binding, the other with a maleimide for reaction with thiol and a cyclooctyne moiety for ligation with copper-free click chemistry. In general, the compounds are red to orange, fluorescent materials with an absorption at about 450 nm and an emission at 560 nm with quantum yields between 2–41 %. Of particular interest is the maleimide- functionalized compound, which shows low fluorescence quantum yield (2%) by itself. After addition of a thiol, the fluorescence is “turned on”; quantum yield 41%.
机译:二苯二甲酸酯是荧光染料并限定支架,其可以在其两个羧酸盐残基上与轴承任务特异性反应性基团的功能残留物正交官能化。 报道了用硫醇基团的单官能化染料的合成,用于咔嗒化学的叠氮化物,以及用于链霉抗生物素蛋白结合的生物键合的Congener。 制备了两种双官能化染料:一种用叠氮化物,用于点击化学和用于链霉抗生物素蛋白结合的生物素,另一种用马来酰亚胺与硫醇反应,并用无铜的咔哒化化学反应。 通常,该化合物是红色至橙色的荧光材料,在约450nm处的吸收和560nm的发射,量子产率在2-41%之间。 特别感兴趣的是马来酰亚胺官能化化合物,其本身表示低荧光量子产率(2%)。 加入硫醇后,荧光“开启”; 量子产率41%。

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