ArticleAngewandte Chemie (International ed. in English)2022
Synthesis of 20-Membered Macrocyclic Pseudo-Natural Products Yields Inducers of LC3 Lipidation.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 20 citations in OpenAlex.
- Pseudonatural Products for Chemical Biology and Drug Discovery.Journal of medicinal chemistry · 2025Review
- Unifying principles for the design and evaluation of natural product-inspired compound collections.Chemical science · 2025Review
- Dimeric natural product panepocyclinol A inhibits STAT3Acta pharmaceutica Sinica. B · 2025Article
- A chemical inhibitor of IST1-CHMP1B interaction impairs endosomal recycling and induces noncanonical LC3 lipidation.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- Targeted sampling of natural product space to identify bioactive natural product-like polyketide macrolides.Nature communications · 2024Article
- The Time and Place for Nature in Drug Discovery.JACS Au · 2022Review
- Synthesis of 20-Membered Macrocyclic Pseudo-Natural Products Yields Inducers of LC3 Lipidation.Angewandte Chemie (International ed. in English) · 2022Article
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Authors and funding
9 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Design and synthesis of pseudo-natural products (PNPs) through recombination of natural product (NP) fragments in unprecedented arrangements enables the discovery of novel biologically relevant chemical matter. With a view to wider coverage of NP-inspired chemical and biological space, we describe the combination of this principle with macrocycle formation. PNP-macrocycles were synthesized efficiently in a stereoselective one-pot procedure including the 1,3-dipolar cycloadditions of different dipolarophiles with dimeric cinchona alkaloid-derived azomethine ylides formed in situ. The 20-membered bis-cycloadducts embody 18 stereocenters and an additional fragment-sized NP-structure. After further functionalization, a collection of 163 macrocyclic PNPs was obtained. Biological investigation revealed potent inducers of the lipidation of the microtubule associated protein 1 light chain 3 (LC3) protein, which plays a prominent role in various autophagy-related processes.
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