ArticleJournal of the American Chemical Society2019
Stereodivergent, Chemoenzymatic Synthesis of Azaphilone Natural Products.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed.
- Asymmetric Ketone Diene Coupling via Stereodivergent Copper Catalysis.Journal of the American Chemical Society · 2026Article
- Minutellins E-I and daldinone L, new secondary metabolites from different species of the Hypoxylaceae (Xylariales, Ascomycota).Mycology · 2026Article
- Article
- Advanced Technologies for Large Scale Supply of Marine Drugs.Marine drugs · 2025Review
- Substrate-Multiplexed Assessment of Aromatic Prenyltransferase Activity.Chembiochem : a European journal of chemical biology · 2025Article
- Ancestral Sequence Reconstruction to Enable Biocatalytic Synthesis of Azaphilones.Journal of the American Chemical Society · 2024Article
- Review
- Intein-mediated temperature control for complete biosynthesis of sanguinarine and its halogenated derivatives in yeast.Nature communications · 2024Article
- Miniaturized Cultivation Profiling (MATRIX)-Facilitated Discovery of Noonazines A-C and Noonaphilone A from an Australian Marine-Derived Fungus,Marine drugs · 2024Article
- The Impact of Metagenomics on Biocatalysis.Angewandte Chemie (International ed. in English) · 2024Review
- Substrate-Selective Catalysis Enabled Synthesis of Azaphilone Natural Products.ACS central science · 2024Article
- Biocatalytic Stereoselective Oxidation of 2-Arylindoles.Journal of the American Chemical Society · 2024Article
- Guiding discovery of protein sequence-structure-function modeling.Bioinformatics (Oxford, England) · 2024Article
- Engineered and total biosynthesis of fungal specialized metabolites.Nature reviews. Chemistry · 2024Review
- Recent Developments and Applications of Biocatalytic and Chemoenzymatic Synthesis for the Generation of Diverse Classes of Drugs.Current pharmaceutical biotechnology · 2024Article
- RetroBioCat Database: A Platform for Collaborative Curation and Automated Meta-Analysis of Biocatalysis Data.ACS catalysis · 2023Article
- Review
- Charting the Evolution of Chemoenzymatic Strategies in the Syntheses of Complex Natural Products.Journal of the American Chemical Society · 2023Review
- Deciphering the evolution of flavin-dependent monooxygenase stereoselectivity using ancestral sequence reconstruction.Proceedings of the National Academy of Sciences of the United States of America · 2023Article
- Article
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Authors and funding
7 authors.
Funding
Abstract
Selective access to a targeted isomer is often critical in the synthesis of biologically active molecules. Whereas small-molecule reagents and catalysts often act with anticipated site- and stereoselectivity, this predictability does not extend to enzymes. Further, the lack of access to catalysts that provide complementary selectivity creates a challenge in the application of biocatalysis in synthesis. Here, we report an approach for accessing biocatalysts with complementary selectivity that is orthogonal to protein engineering. Through the use of a sequence similarity network (SSN), a number of sequences were selected, and the corresponding biocatalysts were evaluated for reactivity and selectivity. With a number of biocatalysts identified that operate with complementary site- and stereoselectivity, these catalysts were employed in the stereodivergent, chemoenzymatic synthesis of azaphilone natural products. Specifically, the first syntheses of trichoflectin, deflectin-1a, and lunatoic acid A were achieved. In addition, chemoenzymatic syntheses of these azaphilones supplied enantioenriched material for reassignment of the absolute configuration of trichoflectin and deflectin-1a based on optical rotation, CD spectra, and X-ray crystallography.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.