Abstract
Unprotected l-phenylalanine was derivatized by an innovative enzymatic method by means of laccases from Pycnoporus cinnabarinus and Myceliophthora thermophila. During the incubation of l-phenylalanine with para-hydroquinones using laccase as biocatalyst, one or two main products were formed. Dependent on the substitution grade of the hydroquinones mono- and diaminated products were detected. Differences of the used laccases are discussed. The described reactions are of interest for the derivatization of amino acids and a synthesis of pharmacological-active amino acid structures in the field of white biotechnology.
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Acknowledgments
Financial support by means of a scholarship from the government of Mecklenburg-Vorpommern is gratefully acknowledged. We thank M. Lalk (Institute of Pharmacy, University of Greifswald), K. Weisz (Institute of Biochemistry, University of Greifswald) for providing NMR data and R. Jack (Institute of Immunology, University of Greifswald) for help in preparing the manuscript.
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Hahn, V., Mikolasch, A., Manda, K. et al. Laccase-catalyzed carbon–nitrogen bond formation: coupling and derivatization of unprotected l-phenylalanine with different para-hydroquinones. Amino Acids 37, 315–321 (2009). https://doi.org/10.1007/s00726-008-0154-2
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DOI: https://doi.org/10.1007/s00726-008-0154-2