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Published on: July 6, 2012
D3h -Symmetrical Shape-Persistent Macrocycles Consisting of Pyridine-Acetylene-Phenol Conjugates as an Efficient Host
Hajime Abe1, Tetsuhiro Yoneda1, Yuki Ohishi1
1Graduate School of Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama, 930-0194, Japan.
Abstract:
Hexagonal shape-persistent macrocycles (SPMs) consisting of three pyridine and three phenol rings linked with acetylene bonds were developed as a preorganized host for saccharide recognition by push-pull-type hydrogen bonding. Three tert-butyl or 2,4,6-triisopropylphenyl substituents were introduced on the host to suppress self-aggregation by steric hindrance. In spite of the simple architecture, association constants Ka of the host with alkyl glycoside guests reached the order of 106 m-1 on the basis of UV/Vis titration experiments. This glycoside recognition was much stronger than that in the cases of acyclic equivalent hosts because of the entropic advantage brought by preorganization of the hydrogen-bonding sites. Solid-liquid extraction and liquid-liquid transport through a liquid membrane were demonstrated by using native saccharides, and much preference to mannose was observed.
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