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Orthogonally Protected Diaminoterephthalate Scaffolds: Installation of Two Functional Units at the Chromophore
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2018-03-13 00:00:00 , DOI: 10.1021/acs.joc.8b00347
Leon Buschbeck 1 , Jens Christoffers 1
Affiliation  

The 2,5-diaminoterephthalate structural motif is a powerful chromophore with remarkable fluorescence properties. Containing two carboxylate and two amino functions, it defines a colored molecular scaffold which allows for orthogonal functionalization with different functional units. Therefore, different applications in life sciences and materials science could be addressed. In this study, the two amino functions were alkylated by reductive amination with side chains carrying amino (orthogonally protected as Boc or Alloc) and carboxylate functions (orthogonally protected as tBu or allyl ester). After sequential deprotections, functional units were introduced by amidation reactions. As three examples, the chromophore was coupled with retinoic acid and fullerene C60 in order to obtain a triad for studying photoinduced electron transfer processes. Furthermore, cyclooctyne and azide moieties were introduced as functional units, allowing for ligation by click reactions. These two clickable groups were applied in combination with maleimide units which are reactive toward thiol residues. The latter dyes define so-called “turn on” probes, since the fluorescence quantum yields increased by one order of magnitude upon reaction with the molecular target.

中文翻译:

正交保护的二氨基对苯二酸酯支架:在发色团上安装两个功能单元

2,5-二氨基对苯二甲酸酯的结构基序是一种功能强大的发色团,具有出色的荧光特性。它包含两个羧酸盐和两个氨基官能团,它定义了一个有色分子支架,该支架可以与不同的功能单元进行正交官能化。因此,可以解决生命科学和材料科学中的不同应用。在这项研究中,两个氨基官能团通过带有氨基的侧链(氨基被正交保护为Boc或Alloc)和羧酸盐官能团(正交被保护为t Bu或烯丙基酯)的还原胺化而烷基化。顺序脱保护后,通过酰胺化反应引入功能单元。作为三个实例,发色团与视黄酸和富勒烯C 60偶联。为了获得用于研究光致电子转移过程的三元组。此外,将环辛炔和叠氮基部分作为功能单元引入,从而允许通过点击反应进行连接。将这两个可点击的基团与对硫醇残基具有反应性的马来酰亚胺单元组合使用。后一种染料定义了所谓的“开启”探针,因为与分子靶反应后,荧光量子产率提高了一个数量级。
更新日期:2018-03-13
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