Slightly congested amino terminal dendrimers. The synthesis of amide-based stable structures on a large scale,Polymer Chemistry

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Slightly congested amino terminal dendrimers. The synthesis of amide-based stable structures on a large scale
Polymer Chemistry ( IF 4.1 ) Pub Date : 2021-08-17 , DOI: 10.1039/d1py00667c
Anjara Morgado _{1,

2} , Francisco Najera _{1,

2} , Anna Lagunas _{3,

4} , Josep Samitier _{3,

4,

5} , Yolanda Vida _{1,

2} , Ezequiel Perez-Inestrosa _{1,

2}

Affiliation

Nowadays, amino terminal dendrimers are appealing materials for biological applications due to their multivalence and the versatile conjugation of the amino groups. However, the high reactivity of these terminal groups can be decreased by steric hindrance, limiting their possible bioapplications. Herein, we report the divergent synthesis of slightly sterically hindered amino terminal polyamide dendrimers. A simple and unique AB₂ scaffold has been chosen to build the dendritic structures, where only amide bonds have been used as the connecting unit. The 1–7 relative positions of the amino groups in the AB₂ monomers avoid the steric congestion of the macromolecules, allowing the construction of robust dendrimers up to the fifth generation. The construction of the dendrimers is based on two well-established reactions, using simple and cheap reactants, with yields above 90% on a gram scale and easy purification procedures. This synthetic methodology constitutes an easy and efficient way for the preparation of stable and aqueous soluble dendrimers on a gram scale, representing a substantial improvement over the synthesis of this kind of aliphatic polyamide amino terminal dendrimer. The prepared structures were completely characterized and evaluated by size exclusion chromatography, diffusion ordered spectroscopy and atomic force microscopy to determine their size. Molecular dynamics simulations were also carried out and the values obtained were consistent with the experimentally determined values.

中文翻译：

略微拥挤的氨基末端树枝状聚合物。大规模合成基于酰胺的稳定结构

如今，氨基末端树枝状聚合物因其多价性和氨基的多功能共轭性而成为生物应用的有吸引力的材料。然而，空间位阻会降低这些末端基团的高反应性，从而限制了它们可能的生物应用。在此，我们报告了略微空间位阻的氨基末端聚酰胺树枝状聚合物的发散合成。选择了一种简单而独特的 AB ₂支架来构建树枝状结构，其中仅使用酰胺键作为连接单元。AB _{2 中}氨基的 1-7 个相对位置单体避免了大分子的空间拥塞，允许构建坚固的树枝状聚合物，直至第五代。树枝状聚合物的构建基于两个成熟的反应，使用简单且廉价的反应物，克级产率超过 90%，且纯化程序简单。这种合成方法构成了一种以克规模制备稳定和水溶性树枝状大分子的简单有效的方法，代表了对这种脂肪族聚酰胺氨基末端树枝状大分子的合成的实质性改进。通过尺寸排阻色谱、扩散有序光谱和原子力显微镜完全表征和评估制备的结构以确定它们的尺寸。

更新日期：2021-08-25

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