Related Experiment Video
Updated: Feb 8, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Trifunctional flavoenzyme-catalyzed asymmetric 4-alkyl-butenolide assembly in avenolide biosynthesis
Wenrui Li1,2, Jinlian Zhao1, Weibo Zeng1,3
1State Key Laboratory of Microbial Diversity and Innovative Utilization, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China.
Abstract:
Butenolides are important features of many bioactive compounds. Current petrochemical-based methods for asymmetric butenolide synthesis are unsustainable. Biocatalysis could enable cheaper, greener, and more sustainable alternatives. However, known butenolide biosynthetic pathways are complex and challenging to harness. Here we show that avenolide, a 4-alkylbutenolide that regulates avermectin production in Streptomyces avermitilis, is assembled from a fatty acyl thioester by a multifunctional flavoenzyme and an iterative cytochrome P450. The flavoenzyme catalyzes homochiral 4-alkylbutenolide formation via successive desaturation, hydroxylation, and lactonization reactions, using dioxygen as the sole stoichiometric reagent. This lays the foundation for development of sustainable biocatalytic asymmetric butenolide synthesis.
Related Concept Videos
Biosynthesis in Bacteria
Biosynthesis of Polysaccharides
Biosynthesis of Lipids
Rotation of Asymmetric Top
The relationship between the angular momentum of any rigid body and its angular velocity, both of which are vectors, involves the moment of inertia. The moment of inertia is a scalar quantity only for spherically symmetric...
Biosynthesis of Nucleic Acids
Asymmetric Lipid Bilayer

