Laccase-catalyzed carbon-nitrogen bond formation: coupling and derivatization of unprotected L-phenylalanine with different para-hydroquinones

Amino Acids. 2009 Jul;37(2):315-21. doi: 10.1007/s00726-008-0154-2. Epub 2008 Aug 10.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry
  • Carbon / metabolism*
  • Fungal Proteins / metabolism*
  • Hydroquinones* / chemistry
  • Hydroquinones* / metabolism
  • Laccase / metabolism*
  • Molecular Structure
  • Nitrogen / chemistry*
  • Phenylalanine* / chemistry
  • Phenylalanine* / metabolism
  • Pycnoporus / enzymology

Substances

  • Fungal Proteins
  • Hydroquinones
  • Phenylalanine
  • Carbon
  • Laccase
  • Nitrogen