Synthesis of Cyclophane Oligomers Having Multivalently Enhanced Guest-Binding Affinity Based on Cluster Effect

水溶性环蕃二聚体、三聚体、四聚体和五聚体是通过用赖氨酸和相应的赖氨酸肽作为支架氨解四氮杂[6.1.6.1]对环蕃的琥珀酰亚胺基酯衍生物，然后除去保护基团来制备的。本环蕃低聚物显示出增强的客人结合亲和力对荧光客人，如6-对甲苯胺基-萘-2-磺酸酯，与那些单环环蕃相比，反映在大环的多价效应。SPR测量也证实了多价大环化合物对本环蕃低聚物的客体结合的影响。

Water-soluble cyclophane dimer, trimer, tetramer, and pentamer were prepared by aminolysis of succinimidyl ester derivative of tetraaza[6.1.6.1] paracyclophane with lysine and the corresponding lysine peptide as a scaffold, followed by removal of the protecting groups. The present cyclophane oligomers showed enhanced guest-binding affinities toward fluorescent guests such as 6-p-toluidino-naphthalene-2-sulfonate, in comparison with those of monocyclic cyclophane, reflecting multivalency effects in macrocycles. The effects of multivalent macrocycles on the guest-binding of the present cyclophane oligomers were also confirmed by SPR measurements.