TY - JOUR
T1 - Molecular recognition by novel cage-type azaparacyclophanes bearing chiral binding sites in aqueous media
AU - Murakami, Yukito
AU - Hayashida, Osamu
AU - Ito, Toshihiro
AU - Hisaeda, Yoshio
PY - 1993/1/1
Y1 - 1993/1/1
N2 - Novel cage-type cyclophanes which are constructed with two rigid macrocyclic skeletons, tetraaza[6.1.6.1]paracyclophane and tetraaza[3.3.3.3]-paracyclophane, and four chiral bridging components were prepared. An asymmetric character of the internal cavity was clarified by means of circular dichroism (CD) spectroscopy and a computer-aided molecular modeling study based on molecular mechanics and dynamics (BIOGRAF, Dreiding-I and Dreiding-II) conformational search. In aqueous media, the present hosts strongly bound anionic and nonionic hydrophobic guests to form inclusion complexes in 1:1 stoichiometry and the CD phenomena were induced in an incorporated achiral guest molecule through its stereochemical interaction with the chiral host cavity. In addition, the present hosts exhibited discriminative recognition toward steroid hormones in D2O/CD3OD (3:1 v/v) as effected by hydrophobic and π-π interactions. The chirality-based discrimination of estrogens was attributed to their different modes of hydrogen bonding with the hosts.
AB - Novel cage-type cyclophanes which are constructed with two rigid macrocyclic skeletons, tetraaza[6.1.6.1]paracyclophane and tetraaza[3.3.3.3]-paracyclophane, and four chiral bridging components were prepared. An asymmetric character of the internal cavity was clarified by means of circular dichroism (CD) spectroscopy and a computer-aided molecular modeling study based on molecular mechanics and dynamics (BIOGRAF, Dreiding-I and Dreiding-II) conformational search. In aqueous media, the present hosts strongly bound anionic and nonionic hydrophobic guests to form inclusion complexes in 1:1 stoichiometry and the CD phenomena were induced in an incorporated achiral guest molecule through its stereochemical interaction with the chiral host cavity. In addition, the present hosts exhibited discriminative recognition toward steroid hormones in D2O/CD3OD (3:1 v/v) as effected by hydrophobic and π-π interactions. The chirality-based discrimination of estrogens was attributed to their different modes of hydrogen bonding with the hosts.
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U2 - 10.1351/pac199365030551
DO - 10.1351/pac199365030551
M3 - Article
AN - SCOPUS:49549084677
SN - 0033-4545
VL - 65
SP - 551
EP - 556
JO - Pure and Applied Chemistry
JF - Pure and Applied Chemistry
IS - 3
ER -