Carofiglio T, Fornasier R, Lucchini V, Simonato L, Tonellato U
double daggerDipartimento di Chimica Inorganica, Università di Padova, Via Marzolo 1, 35100 Padova, Italy.
J Org Chem. 2000 Dec 29;65(26):9013-21. doi: 10.1021/jo0010678.
Reductive amination of 6-deoxy-6-formyl-beta-cyclodextrin with 5-(p-aminophenyl)-10,15,20-tris(p-sulfonatophenyl)porphyrin in the presence of an excess of sodium cyanoborohydride affords the hydrophilic cyclodextrin-porphyrin conjugate 3 in 23% yield. The structure of 3 was confirmed by NMR spectroscopy and mass spectrometry techniques. Compound 3 showed a marked tendency to dimerize in aqueous conditions via the formation of intermolecular porphyrin-cyclodextrin inclusion complexes and/or through electrostatic interactions. Information on the structure of these aggregates has been obtained by the use of circular dichroism and UV-vis spectroscopy. Aggregation can be avoided by the use of heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin (TM beta CD) that forms a 1:1 inclusion complex with compound 3.
在过量氰基硼氢化钠存在下，6-脱氧-6-甲酰基-β-环糊精与5-(对氨基苯基)-10,15,20-三(对磺酸钠苯基)卟啉进行还原胺化反应，以23%的产率得到亲水性环糊精-卟啉共轭物3。通过核磁共振光谱和质谱技术确定了3的结构。化合物3在水性条件下通过形成分子间卟啉-环糊精包合物和/或通过静电相互作用表现出明显的二聚倾向。通过使用圆二色光谱和紫外-可见光谱获得了这些聚集体结构的信息。通过使用与化合物3形成1:1包合物的七(２,３,６-三-Ｏ-甲基)-β-环糊精(TMβCD)可以避免聚集。
