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

Research output: Contribution to journalArticle

14 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

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Bearings (structural)
Circular dichroism spectroscopy
Dipeptides
Circular Dichroism
Spectrum Analysis
Binding Sites
Fluorescence Polarization
Skeleton
Fluorescence
Nuclear magnetic resonance
Polarization
Molecules
pamoic acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Preparation and host-guest interactions of novel cage-type cyclophanes bearing chiral binding sites provided by dipeptide residues. / Tanaka, Akinori; Fujiyoshi, Setsuko; Motomura, Koji; Hayashida, Osamu; Hisaeda, Yoshio; Murakami, Yukito.

In: Tetrahedron, Vol. 54, No. 20, 14.05.1998, p. 5187-5206.

Research output: Contribution to journalArticle

Tanaka, Akinori ; Fujiyoshi, Setsuko ; Motomura, Koji ; Hayashida, Osamu ; Hisaeda, Yoshio ; Murakami, Yukito. / Preparation and host-guest interactions of novel cage-type cyclophanes bearing chiral binding sites provided by dipeptide residues. In: Tetrahedron. 1998 ; Vol. 54, No. 20. pp. 5187-5206.
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