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Preparation of a β-Cyclodextrin-Modified N-Carboxymethylchitosan and Its Chromatographic Behavior as a Chiral HPLC Stationary Phase

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Abstract

Chitosan, whose deacetylation degree was 0.95, was N-carboxymethylated and subsequently modified with 6-amino-6-deoxy-β-cyclodextrin. The 1H NMR spectra of the carboxymethylated chitosan (NCMC) and the β-cyclodextrin-modified NCMC (β-CD-NCMC) showed introductions of ca. 8.4 of the carboxymethyl groups and 8.2 of β-CD moieties per 10 units, respectively. β-CD-NCMC was covalently attached to a macroporous silica gel and used as a stationary phase for chiral HPLC separations of 2, 4-dinitrophenyl-α-amino acids and related racemates. The chiral discrimination was influenced more strongly by the size of an alkyl group on the chiral center of the aliphatic amino acids, compared to a Cyclobond I bearing monomeric β-CD molecules. The distance between two aromatic moieties on the aromatic amino acids and related racemates was also discriminated. The strict recognition required the high substitution degree of the β-CD moiety, permitting us to propose a simultaneous inclusion of the 2,4-dinitrophenyl group and another aromatic substituent or an alkyl group with a proper size into the two adjacent CD cavities on the polymer chain.

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Authors and Affiliations

  1. Department of Applied Chemistry, Faculty of Engineering, Oita University, Dannoharu, Oita, 870-11, Japan

    Yoshiaki Kurauchi, Hiroyoshi Ono, Bo Wang, Naoyoshi Egashiba & Kazuya Ohga

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  1. Yoshiaki Kurauchi
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  2. Hiroyoshi Ono
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  3. Bo Wang
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  4. Naoyoshi Egashiba
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  5. Kazuya Ohga
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Kurauchi, Y., Ono, H., Wang, B. et al. Preparation of a β-Cyclodextrin-Modified N-Carboxymethylchitosan and Its Chromatographic Behavior as a Chiral HPLC Stationary Phase. ANAL. SCI. 13, 47–52 (1997). https://doi.org/10.2116/analsci.13.47

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  • DOI: https://doi.org/10.2116/analsci.13.47

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