Enantiocomplementary Dirigent Protein for the Enantioselective Laccase-Catalyzed Oxidative Coupling of Phenols

(+)‐ 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)....

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Published in:Angewandte Chemie (International ed.) 2010-01, Vol.49 (1), p.202-204
Main Authors: Pickel, Benjamin, Constantin, Mihaela-Anca, Pfannstiel, Jens, Conrad, Jürgen, Beifuss, Uwe, Schaller, Andreas
Format: Article
Language:English
Subjects:
Amino Acid Sequence
arabidopsis
Arabidopsis Proteins - chemistry
Arabidopsis Proteins - isolation & purification
Arabidopsis Proteins - metabolism
Biocatalysis
dirigent proteins
enantioselectivity
Furans - chemistry
Laccase - chemistry
Laccase - metabolism
lignans
Lignans - biosynthesis
Lignans - chemistry
Molecular Sequence Data
Oxidation-Reduction
phenol couplings
Phenols - chemistry
Plant Proteins - chemistry
Plant Proteins - isolation & purification
Plant Proteins - metabolism
Sequence Alignment
Sequence Homology, Amino Acid
Stereoisomerism
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Summary:(+)‐ 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200904622