Departamento de Química Orgánica, Facultad de Química, Universidad Complutense de Madrid , E-28040 Madrid, Spain.
Instituto de Investigaciones Químicas (IIQ), CSIC - Universidad de Sevilla , Américo Vespucio 49, 41092 Seville, Spain.
J Org Chem. 2018 Feb 16;83(4):1727-1736. doi: 10.1021/acs.joc.7b02402. Epub 2018 Feb 2.
The synthesis of multivalent systems based on hexakis-adducts of [60]fullerene employing a biocompatible copper-free click chemistry strategy has been accomplished. A symmetric hexakis-adduct of fullerene bearing 12 maleimide units (3) is reported, and it has been employed to carry out the thiol-maleimide Michael addition. To achieve orthogonal click addition, an asymmetric derivative bearing one maleimide and 10 cyclooctynes has been synthesized. The sequential and one-pot transformations of the two clickable groups have been explored, finding the best results in the case of the one-pot experiment. This route has been used to obtain a biocompatible hexakis-adduct appended with two different biomolecules, carbohydrates, and amino acids.
采用生物相容性的无铜点击化学策略，完成了基于[60]富勒烯六加成物的多价体系的合成。报道了一种具有 12 个马来酰亚胺单元的对称六加成 fullerene（3），并将其用于巯基-马来酰亚胺迈克尔加成反应。为了实现正交点击加成，合成了带有一个马来酰亚胺和 10 个环辛炔的不对称衍生物。探索了两个可点击基团的顺序和一锅转化，在一锅实验的情况下得到了最佳结果。该路线已用于获得生物相容性的六加成物，其连接有两种不同的生物分子，碳水化合物和氨基酸。
