Wallisch Melanie, Sulmann Stefan, Koch Karl-Wilhelm, Christoffers Jens
Institut für Chemie, Carl von Ossietzky-Universität Oldenburg, 26111, Oldenburg, Germany.
Biochemistry Group, Department of Neuroscience, Carl von Ossietzky-Universität Oldenburg, 26111, Oldenburg, Germany.
Chemistry. 2017 May 11;23(27):6535-6543. doi: 10.1002/chem.201700774. Epub 2017 Apr 6.
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 %.
二氨基对苯二甲酸酯是荧光染料并定义了支架，其可以在两个羧酸酯残基处用带有特定任务反应性基团的功能性残基进行正交功能化。本文报道了用于表面结合的含硫醇基团的单功能化染料、用于点击化学的叠氮化物以及用于链霉亲和素结合的生物素化同系物的合成。制备了两种双功能化染料：一种带有用于点击化学的叠氮化物和用于链霉亲和素结合的生物素，另一种带有用于与硫醇反应的马来酰亚胺和用于无铜点击化学连接的环辛炔部分。一般来说，这些化合物是红色至橙色的荧光材料，在约450 nm处有吸收，在560 nm处有发射，量子产率在2 - 41%之间。特别令人感兴趣的是马来酰亚胺功能化的化合物，其本身显示出低荧光量子产率（2%）。加入硫醇后，荧光“开启”；量子产率为41%。
