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β-Cyclodextrin PAMAM dendrimer: how to overcome the tumbling process for getting fully available host cavities
European Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2020-02-20 , DOI: 10.1002/ejoc.201901823
Israel González-Méndez 1 , Aurélien Hameau 2, 3 , Régis Laurent 2, 3 , Christian Bijani 2, 3 , Valérie Bourdon 4 , Anne-Marie Caminade 2, 3 , Ernesto Rivera 1 , Kathleen I. Moineau-Chane Ching 2, 3
Affiliation  

The synthesis of a G0 polyamidoamide (PAMAM) dendrimer end-capped with four β-cyclodextrin (β-CD) units, named as Tetra-CD was performed by using copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC). This new platform presents a considerable high water-solubility in comparison to native β-CD. Tumbling process involving half of the CD cavities in D2O was evidenced by 1H NMR spectroscopy. Interaction of adamantane with Tetra-CD has been fully investigated by 1D/2D NMR techniques and mass spectrometry besides a joint study on new β-CD monomers (named as A and B) and on a dimer (Di-CD) and a trimer (Tri-CD). The obtained results demonstrate that the tumbling effect can be shifted in the presence of an appropriate hydrophobic guest resulting in the full host-ability of the CD units in water for that guest.

中文翻译:

β-环糊精 PAMAM 树枝状聚合物:如何克服翻滚过程以获得完全可用的宿主腔

通过使用铜 (I) 催化的炔-叠氮化物环加成 (CuAAC) 合成了以四个 β-环糊精 (β-CD) 单元封端的 G0 聚酰胺酰胺 (PAMAM) 树枝状聚合物,命名为 Tetra-CD。与天然 β-CD 相比,这种新平台具有相当高的水溶性。1H NMR 光谱证实了涉及 D2O 中一半 CD 腔的翻滚过程。除了对新的 β-CD 单体(命名为 A 和 B)以及二聚体 (Di-CD) 和三聚体的联合研究外,还通过 1D/2D NMR 技术和质谱法对金刚烷与 Tetra-CD 的相互作用进行了全面研究(三张光盘)。获得的结果表明,在适当的疏水客体存在的情况下,翻滚效应可以改变,从而导致 CD 单元在水中对那个客体具有完全的主体能力。
更新日期:2020-02-20
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