Universidad de Málaga-IBIMA , Departamento de Química Orgánica , Campus de Teatinos s/n , 29071 Málaga , Spain.
Centro Andaluz de Nanomedicina y Biotecnología-BIONAND , Parque Tecnológico de Andalucı́a , C/ Severo Ochoa 35 , 29590 , Campanillas, Málaga , Spain.
J Org Chem. 2019 Aug 16;84(16):10197-10208. doi: 10.1021/acs.joc.9b01369. Epub 2019 Jul 29.
Herein, we present an easy and efficient synthesis of amino terminal dendrons, combining protection/deprotection reactions with copper-catalyzed azide alkyne cycloaddition in a convergent way. This new approach affords dendrons in gram scale with excellent yields and easy purification. By choosing the appropriate azido-functionalized core, these dendrons lead to a more efficient and controlled convergent synthesis of dendrimers with different sizes and shapes and multivalence. The amino terminal dendrimers were analyzed by diffusion-ordered spectroscopy experiments. The observed dendrimer size is in excellent correlation with the expected size and shape by molecular dynamic simulations. The construction of these kinds of nanostructures, in a simple and efficient way, opens new opportunities for biomedical applications. Moreover, by choosing the appropriate core, these versatile macromolecules become an excellent fluorescent biomarker.
在此，我们提出了一种简单有效的方法来合成氨基末端树突，该方法通过保护/脱保护反应与铜催化的叠氮-炔环加成反应相结合，以收敛的方式进行。这种新方法可以在克级规模下以优异的收率和易于纯化的方式得到树突。通过选择适当的叠氮功能化核心，这些树突可以更有效地控制不同大小和形状以及多价的树枝状大分子的收敛合成。通过扩散排序光谱实验对氨基末端树枝状大分子进行了分析。观察到的树枝状大分子的大小与分子动力学模拟所预期的大小和形状非常吻合。以简单有效的方式构建这些纳米结构为生物医学应用开辟了新的机会。此外，通过选择适当的核心，这些多功能的大分子成为了出色的荧光生物标志物。
