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Chiral separation of d/l-aldoses by micellar electrokinetic chromatography using a chiral derivatization reagent and a phenylboronic acid complex

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Abstract

A novel method was developed for d/l-isomeric separation of aldopentoses and aldohexoses as their (S)-(+)-4-(N,N-dimethylaminosulfonyl)-7-(3-aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole derivatives using phenylboronate buffer containing sodium dodecyl sulfate as a background electrolyte. The combination of derivatization with a chiral labeling reagent and micellar electrokinetic chromatography with phenylboronate made possible the efficient separation of d/l isomers as well as epimeric isomers of aldopentoses and aldohexoses. Laser-induced fluorescence detection permitted the micromolar-level determination of monosaccharide derivatives. The limit of detection was 105 amol (300 nM), and the repeatabilities of the migration times and peak area responses were 0.8 % and 7.9 % (relative standard deviation; n = 6), respectively. The method was applied to the determination of d/l- galactose in red seaweed.

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Acknowledgments

This work was supported in part by a Grant-in-Aid for Scientific Research from the Japan Society for the Promotion of Science and by the “Antiaging Center Project” for Private Universities from the Ministry of Education, Culture, Sports, Science and Technology, 2013–2014.

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi, Osaka, 577-8502, Japan

    Sachio Yamamoto, Yoko Tamata, Kaori Sejima, Mitsuhiro Kinoshita & Shigeo Suzuki

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  1. Sachio Yamamoto
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  2. Yoko Tamata
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  3. Kaori Sejima
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  4. Mitsuhiro Kinoshita
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  5. Shigeo Suzuki
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Correspondence to Sachio Yamamoto.

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Yamamoto, S., Tamata, Y., Sejima, K. et al. Chiral separation of d/l-aldoses by micellar electrokinetic chromatography using a chiral derivatization reagent and a phenylboronic acid complex. Anal Bioanal Chem 407, 6201–6206 (2015). https://doi.org/10.1007/s00216-015-8802-3

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  • DOI: https://doi.org/10.1007/s00216-015-8802-3

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