Biosynthesis of the Prenylated Salicylaldehyde Flavoglaucin Requires Temporary Reduction to Salicyl Alcohol for Decoration before Reoxidation to the Final Product
Jonas Nies, Huomiao Ran, Viola Wohlgemuth, Wen‐Bing Yin, Shu‐Ming Li
Abstract
The biosynthetic pathway of the prenylated salicylaldehyde flavoglaucin and congeners in Aspergillus ruber was elucidated by genome mining, heterologous expression, precursor feeding, and biochemical characterization. The polyketide skeleton was released as alkylated salicyl alcohols, which is a prerequisite for consecutive hydroxylation and prenylation, before reoxidation to the final aldehyde products. Our results provide an excellent example for a highly programmed machinery in natural product biosynthesis.
Topics & Concepts
PrenylationChemistrySalicylaldehydeBiosynthesisNatural productPolyketideHydroxylationAldehydeAlcoholCombinatorial chemistryStereochemistryOrganic chemistryCatalysisEnzymeSchiff baseMicrobial Natural Products and BiosynthesisPlant biochemistry and biosynthesisNatural product bioactivities and synthesis