Molecular Recognition of Medium-size Lactones by Enclathration of Cholic Acid

Kazuki Sada Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido Gifu, 501-1112, Japan; Department of Applied Chemistry and Applied Fine Chemistry, Faculty of Engineering, Osaka University, Yamadaoka, Suita, Osaka, 565-0871, Japan

Kazunori Nakano Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido Gifu, 501-1112, Japan; Nagoya Municipal Industrial Research Institute, Rokuban, Atsuta-ku, Nagoya, 456-0058, Japan

Kiyoshi Hirayama Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido Gifu, 501-1112, Japan

Mikiji Miyata Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido Gifu, 501-1112, Japan; Department of Material and Life Science, Graduate School of Engineering, Osaka University, Yamadaoka, Suita, Osaka, 565-0871, Japan

Satoshi Sasaki Department of Applied Chemistry and Applied Fine Chemistry, Faculty of Engineering, Osaka University, Yamadaoka, Suita, Osaka, 565-0871, Japan

Kiichi Takemoto Department of Applied Chemistry and Applied Fine Chemistry, Faculty of Engineering, Osaka University, Yamadaoka, Suita, Osaka, 565-0871, Japan

Nobutami Kasai Department of Applied Chemistry and Applied Fine Chemistry, Faculty of Engineering, Osaka University, Yamadaoka, Suita, Osaka, 565-0871, Japan

Kazuaki Kato Department of Material and Life Science, Graduate School of Engineering, Osaka University, Yamadaoka, Suita, Osaka, 565-0871, Japan

Masashi Shigesato Department of Material and Life Science, Graduate School of Engineering, Osaka University, Yamadaoka, Suita, Osaka, 565-0871, Japan

Kunio Miki Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa-oiwake-cho, Sakyo, Kyoto, 606-0745, Japan

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Abstract

Molecular recognitions of medium size lactones by enclathration of cholic acid (CA) are described. Size and location of the substituents on the lactone rings play an important role for enclathration. Lactones within the limited steric dimensions are included in CA, and larger or smaller ones are not included to give guest-free crystals of CA. Moreover, CA partially separates one enantiomer from racemic lactones by recystallization. X-ray crystallographic studies reveal that all included lactones form the β-trans type bilayer structure having a pentagonal void channel with a side pocket. The cross-sections illustrate that the lactone rings are incorporated in the center of the channel and that the substituents of the guests are fixed in the side pockets. The asymmetric channel enables CA to discriminate size and chirality of medium size lactones.

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Molecular Recognition of Medium-size Lactones by Enclathration of Cholic Acid

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Molecular Recognition of Medium-size Lactones by Enclathration of Cholic Acid

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