ArticleJournal of the American Chemical Society2015
New Insights into the Conversion of Versicolorin A in the Biosynthesis of Aflatoxin B1.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 46 citations in OpenAlex.
- Examining Heterodimerization by Aryl C-N Coupling in Dynemicin Biosynthesis.ACS chemical biology · 2023Article
- The 'emodin family' of fungal natural products-amalgamating a century of research with recent genomics-based advances.Natural product reports · 2023Review
- Structural analysis of an anthrol reductase inspires enantioselective synthesis of enantiopure hydroxycycloketones and β-halohydrins.Nature communications · 2023Article
- Enhanced photocatalytic activity of TiORSC advances · 2022Article
- Application of Graphene and its Derivatives in Detecting Hazardous Substances in Food: A Comprehensive Review.Frontiers in chemistry · 2022Review
- Catalytic Control of Spiroketal Formation in Rubromycin Polyketide Biosynthesis.Angewandte Chemie (International ed. in English) · 2021Article
- Aflatoxin Biosynthesis, Genetic Regulation, Toxicity, and Control Strategies: A Review.Journal of fungi (Basel, Switzerland) · 2021Review
- Enzymatic spiroketal formation via oxidative rearrangement of pentangular polyketides.Nature communications · 2021Article
- Xanthones and anthraquinones from the soil fungusRSC advances · 2021Article
- Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi.Chemical science · 2019Article
- Hydroxyl regioisomerization of anthracycline catalyzed by a four-enzyme cascade.Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides.Beilstein journal of organic chemistry · 2016Review
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
A crucial and enigmatic step in the complex biosynthesis of aflatoxin B1 is the oxidative rearrangement of versicolorin A to demethylsterigmatocystin. This step is thought to proceed by an oxidation-reduction-oxidation sequence, in which the NADPH-dependent oxidoreductase AflM catalyzes the enclosed reduction step. AflM from Aspergillus parasiticus, after heterologous production in E. coli and purification, however, catalyzed the reduction of the hydroquinoid form of the starting compound versicolorin A (25% conversion) to a so far unknown product of aflatoxin biosynthesis. The asymmetric reduction of emodin hydroquinone to (R)-3,8,9,10-tetrahydroxy-6-methyl-3,4-dihydroanthracen-1(2H)-one (up to 82% for AflM) has also been observed in previous studies using MdpC from Aspergillus nidulans (monodictyphenone biosynthetic gene cluster). The first (nonenzymatic) reduction of emodin to emodin hydroquinone, for example with sodium dithionite, is obligatory for the enzymatic reduction by AflM or MdpC. These results imply an unprecedented role of AflM in the complex enzymatic network of aflatoxin biosynthesis.
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