Biaryl-Forming Enzymes from Aspergilli Exhibit Substrate-Dependent Stereoselectivity

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Abstract
Natural biaryls typically occur as one regio- and atro-pisomeric variant in a given organism. Here, we report on the identification of biosynthetic genes of aurasperone- and bifonsecin-type biaryls in several As-pergillus species. The genes of the tailoring enzymes form a gene cluster that lies separately from the polyke-tide synthase gene. Dimerization of naphthopyrone monomers is catalyzed by members of an undescribed subfamily of cytochrome P450 enzymes. The stereose-lectivity of these enzymes is influenced by the two natu-ral monomeric substrates; homodimerization of one monomer yields a stereochemically pure biaryl while the other monomer yields a mixture of enantiomers.
Funding Information
  • Deutsche Forschungsgemeinschaft (235777276)

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