ArticleJournal of the American Chemical Society2018
Genome Mining and Assembly-Line Biosynthesis of the UCS1025A Pyrrolizidinone Family of Fungal Alkaloids.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 74 citations in OpenAlex.
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- Elucidation of the pramanicin biosynthetic pathway reveals a DUF2306 family membrane protein involved in terminal epoxidation.Frontiers in microbiology · 2026Article
- The Mutually Inspiring Biological and Chemical Synthesis of Fungal Bicyclo[2.2.2]diazaoctane Indole Alkaloids.Chemical reviews · 2025Review
- Chemoenzymatic Synthesis of 4,5-Dihydroxyisoleucine Fragment of α-Amanitin.Organic letters · 2024Article
- Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-International journal of molecular sciences · 2024Article
- EnzymaticJournal of the American Chemical Society · 2023Article
- Deciphering chemical logic of fungal natural product biosynthesis through heterologous expression and genome mining.Natural product reports · 2023Review
- Late-stage cascade of oxidation reactions during the biosynthesis of oxalicine B inActa pharmaceutica Sinica. B · 2023Article
- Recent Approaches for Downplaying Antibiotic Resistance: Molecular Mechanisms.BioMed research international · 2023Review
- Tricyclic Fused Lactams by Mukaiyama Cyclisation of Phthalimides and Evaluation of their Biological Activity.Antibiotics (Basel, Switzerland) · 2022Article
- Discovery and characterization of a terpene biosynthetic pathway featuring a norbornene-forming Diels-Alderase.Nature communications · 2022Article
- Recent advances in the chemo-biological characterization of decalin natural products and unraveling of the workings of Diels-Alderases.Fungal biology and biotechnology · 2022Review
- Discovery and biosynthesis of macrophasetins from the plant pathogen fungusFrontiers in microbiology · 2022Article
- Molecular Basis for Two Stereoselective Diels-Alderases that Produce Decalin Skeletons*.Angewandte Chemie (International ed. in English) · 2021Article
- Discovery of cyclohexadepsipeptides with anti-Zika virus activities and biosynthesis of the nonproteinogenic building block (3S)-methyl-l-proline.The Journal of biological chemistry · 2021Article
- Discovery and investigation of natural Diels-Alderases.Journal of natural medicines · 2021Review
- Biosynthesis ofJournal of the American Chemical Society · 2021Article
- Chemical and Genetic Studies on the Formation of Pyrrolones During the Biosynthesis of Cytochalasans.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Exploration of Iron- and a-Ketoglutarate-Dependent Dioxygenases as Practical Biocatalysts in Natural Product Synthesis.Synlett : accounts and rapid communications in synthetic organic chemistry · 2021Article
- Predicting the chemical space of fungal polyketides by phylogeny-based bioinformatics analysis of polyketide synthase-nonribosomal peptide synthetase and its modification enzymes.Scientific reports · 2020Article
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Authors and funding
10 authors at 3 institutions in 2 countries.
Funding
Abstract
UCS1025A is a fungal polyketide/alkaloid that displays strong inhibition of telomerase. The structures of UCS1025A and related natural products are featured by a tricyclic furopyrrolizidine connected to a trans-decalin fragment. We mined the genome of a thermophilic fungus and activated the ucs gene cluster to produce UCS1025A at a high titer. Genetic and biochemical analysis revealed a PKS-NRPS assembly line that activates 2S,3S-methylproline derived from l-isoleucine, followed by Knoevenagel condensation to construct the pyrrolizidine moiety. Oxidation of the 3S-methyl group to a carboxylate leads to an oxa-Michael cyclization and furnishes the furopyrrolizidine. Our work reveals a new strategy used by nature to construct heterocyclic alkaloid-like ring systems using assembly line logic.
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