Preparation and host-guest interactions of novel cage-type cyclophanes bearing chiral binding sites provided by dipeptide residues

Akinori Tanaka, Setsuko Fujiyoshi, Koji Motomura, Osamu Hayashida, Yoshio Hisaeda, Yukito Murakami

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    15 Citations (Scopus)

    Abstract

    Novel cage-type cyclophanes, which are constructed with two rigid macrocyclic skeletons, tetraaza[3.3.3.3]paracyclophanes, and four bridging segments composed of either β-L-aspartyl-L-aspartyl or β-D-aspartyl-D- aspartyl residues were prepared [(-)-1 and (+)-1, respectively]. Structural and asymmetric properties of these cage-type cyclophanes were characterized by 1H NMR and circular dichroism (CD) spectroscopy. The guest-binding behavior of the cage-type hosts toward fluorescent guests, such as 8- anilinonapththalene-1-sulfonate and 6-p-toluidinonaphthalene-2-sulfonate, was examined in comparison with those demonstrated by the corresponding non-cage hosts in aqueous media. The microenvironmental polarity around the fluorescent guests and their fluorescence polarization values in the presence of the cage-type hosts revealed that these guest molecules were incorporated into apolar host cavities, and their rotational motion was largely restricted. Furthermore, chiral host-guest interactions between the hosts and a hydrophobic guest, pamoic acid (PA), were examined by CD spectroscopy. PA was subjected to stereochemical changes to assume P- and M-helix configurations in the presence of (-)-1 and (+)-1, respectively.

    Original languageEnglish
    Pages (from-to)5187-5206
    Number of pages20
    JournalTetrahedron
    Volume54
    Issue number20
    DOIs
    Publication statusPublished - May 14 1998

    All Science Journal Classification (ASJC) codes

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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