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Enantioseparation of Aromatic β³-Amino acid by Precolumn Derivatization with o-Phthaldialdehyde and N-Isobutyryl-l-cysteine

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Abstract

In this study we describe the enantioseparation of aromatic β3-amino acids by precolumn derivatization with o-phthaldialdehyde and N-isobutyryl-l-cysteine. Derivatization conditions were studied in detail for (R,S)-β-phenylalanine and (R,S)-β-tyrosine revealing a reaction time of 1 min and a molar ratio of the reagents β³-amino acid to o-phthaldialdehyde to N-isobutyryl-l-cysteine of 1:25:25 as optimal. The method was validated for (R,S)-β-phenylalanine in a bacterial cell extract. The analysis provided excellent specificity and reproducibility. The limit of quantification was 25 pmol per 0.5 μL injection. The method could be successfully transferred to the enantioseparation of other β³-amino acids. Enantioseparation of all studied compounds could be achieved in 4–11 min.

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Acknowledgments

We would like to thank the Federal Ministry of Education and Research for the financial support of this work within the joint project “BioSysPro”: New enzymes and processes for biobased products via the integration of biotechnological and chemical methods. We also thank Olga Lisovaya for her practical input and Anna Suidak for her advice on statistics.

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Authors and Affiliations

  1. Section II: Technical Biology, Institute of Process Engineering in Life Sciences, Karlsruhe Institute of Technology (KIT), Karlsruhe, Germany

    Birgit Brucher, Jens Rudat & Christoph Syldatk

  2. Institute of Biochemical Engineering, University of Stuttgart, Stuttgart, Germany

    Oliver Vielhauer

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  1. Birgit Brucher
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  2. Jens Rudat
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  3. Christoph Syldatk
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  4. Oliver Vielhauer
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Correspondence to Birgit Brucher.

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Brucher, B., Rudat, J., Syldatk, C. et al. Enantioseparation of Aromatic β³-Amino acid by Precolumn Derivatization with o-Phthaldialdehyde and N-Isobutyryl-l-cysteine. Chroma 71, 1063–1067 (2010). https://doi.org/10.1365/s10337-010-1578-x

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  • DOI: https://doi.org/10.1365/s10337-010-1578-x

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