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Keywords:

  • arabidopsis;
  • dirigent proteins;
  • enantioselectivity;
  • lignans;
  • phenol couplings
Thumbnail image of graphical abstract

(+)- or (−)-pinoresinol: that is the question. Which of the two enantiomeric lignans is formed during laccase-catalyzed phenol coupling of (E)-coniferyl alcohol (1) depends on the dirigent protein. In the presence of the first enantiocomplementary dirigent protein AtDIR6, (−)-2 is formed (78 % ee). Preferential formation of (+)-2 is observed in the presence of the dirigent protein FiDIR1, whereas only racemic 2 is formed in the absence of dirigent proteins.