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New Aspects of Cyclodextrin Chemistry Induced by Outside Type Complex Formation; Asymmetric Reduction of Indol-3-Pyruvic Acid with NaBH4 in Aqueous Solution

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Abstract

Asymmetric reduction of indol-3-pyruvic acid (IPA) with NaBH4 in aqueous solution in the presence of various cyclodextrins (α-, β-, γ-, mono-6-amino-6-deoxy-β- and di-6ABamino-6AB-deoxy-β-cyclodextrin) was investigated. From the NMR and circular dichroism spectral studies, the conformation of the CyD–substrate complexes is suggested; the part of carboxylic group stay in the cavity of α-CyD, whole of IPA in β-CyD, two molecules in a γ-CyD cavity, and IPA(s) is/are on the rim of the cavity of mono-6-amino-6-deoxy-β- and di-6ABamino-6AB-deoxy-β-CyD (AβCyD, DAβCyD) with electrostatic interaction between amino group and carboxylic group. This conformational difference provides in the difference in the optical selectivity of reduction.

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Authors and Affiliations

  1. Department of Nano Chemistry, Faculty of Engineering, Tokyo Polytechnic University, Iiyama, Atsugi, Kanagawa, 243-0297, Japan

    KEIKO TAKAHASHI, HIDEKI YOKOMIZO, KATSURO ISHIYAMA, MASAHIKO KITSUTA & MEGUMI OHASHI

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  1. KEIKO TAKAHASHI
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  2. HIDEKI YOKOMIZO
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  3. KATSURO ISHIYAMA
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  4. MASAHIKO KITSUTA
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  5. MEGUMI OHASHI
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Correspondence to KEIKO TAKAHASHI.

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TAKAHASHI, K., YOKOMIZO, H., ISHIYAMA, K. et al. New Aspects of Cyclodextrin Chemistry Induced by Outside Type Complex Formation; Asymmetric Reduction of Indol-3-Pyruvic Acid with NaBH4 in Aqueous Solution. J Incl Phenom Macrocycl Chem 56, 95–99 (2006). https://doi.org/10.1007/s10847-006-9068-3

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  • DOI: https://doi.org/10.1007/s10847-006-9068-3

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