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Laccase-induced derivatization of unprotected amino acid L-tryptophan by coupling with p-hydroquinone 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide

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Summary.

We have studied the enzymatic derivatization of amino acids by use of the polyphenol oxidase laccase. Derivatization of L-tryptophan was achieved by enzymatic crosslinking with the laccase substrate 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide. The main product (yield up to 70%) was identified as the quinoid compound 2-[2-(2-hydroxy-ethylcarbamoyl)-3,6-dioxo-cyclohexa-1,4-dienylamino]-3-(1H-indol-3-yl)- propionic acid and demonstrates that laccase-catalyzed C–N-coupling occurred on the amino group of the aliphatic side chain. These enzyme based reactions provide a simple and fast method for the derivatization of unprotected amino acids.

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Authors and Affiliations

  1. Institut für Mikrobiologie, Ernst-Moritz-Arndt-Universität Greifswald, Greifswald, Germany

    K. Manda, A. Mikolasch & F. Schauer

  2. Laboratory for Functional Genomics, Ernst-Moritz-Arndt-Universität Greifswald, Greifswald, Germany

    E. Hammer

  3. Center for Life Science Automation, Rostock, Germany

    D. Gördes & K. Thurow

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  1. K. Manda
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Manda, K., Hammer, E., Mikolasch, A. et al. Laccase-induced derivatization of unprotected amino acid L-tryptophan by coupling with p-hydroquinone 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide. Amino Acids 31, 409–419 (2006). https://doi.org/10.1007/s00726-005-0276-8

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