Global InformationDirigent protein information
Dirigent proteins are members of a class of proteins which dictate the stereochemistry of a compound synthesized by other enzymes.[1] The first dirigent protein was discovered in Forsythia intermedia. This protein has been found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol monomers:[2]
Lignan biosynthesis is catalysed by oxidative enzymes.[3] In the test tube the reaction results in a heteregenous mixture of dimeric compounds.[4] When a dirigent protein is present during the reaction, one stereoisomer of one compound is highly enriched. Dirigent proteins appear to possess no oxidative radical forming activity of their own; in the absence of oxidative enzyme, no reaction will occur.[5]
Recently, a second, enantiocomplementary dirigent protein was identified in Arabidopsis thaliana, which directs enantioselective synthesis of (-)-pinoresinol.[6]
- ^ Nicholson, Ralph L.; Wilfred Vermerris; Vermerris Wilfred (2006). Phenolic compound biochemistry. Berlin: Springer. pp. 107–108. ISBN 1-4020-5163-8.
- ^ Davin LB, Wang HB, Crowell AL, et al. (1997). "Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center". Science. 275 (5298): 362–6. doi:10.1126/science.275.5298.362. PMID 8994027. S2CID 41957412.
- ^ Ward R.S. (1982). "The synthesis of lignans and neolignans". Chemical Society Reviews. 11 (2): 75–125. doi:10.1039/CS9821100075.
- ^ Fournand D, Cathala B, Lapierre C (January 2003). "Initial steps of the peroxidase-catalyzed polymerization of coniferyl alcohol and/or sinapyl aldehyde: capillary zone electrophoresis study of pH effect". Phytochemistry. 62 (2): 139–46. doi:10.1016/S0031-9422(02)00573-3. PMID 12482448.
- ^ Davin L.B.; Lewis N.G. (August 2005). "Dirigent phenoxy radical coupling: advances and challenges". Current Opinion in Biotechnology. 16 (4): 398–406. doi:10.1016/j.copbio.2005.06.010. PMID 16023845.
- ^ Pickel B, Constantin M-A, Pfannsteil J, Conrad J, Beifuss U, Schaffer A (March 2007). "An Enantiocomplementary Dirigent Protein for the Enantioselective Laccase-Catalyzed Oxidative Coupling of Phenols". Angewandte Chemie. 53 (4): 273–284. doi:10.1007/s10086-007-0892-x. S2CID 195313754.