Synthesis of 20‐Membered Macrocyclic Pseudo‐Natural Products Yields Inducers of LC3 Lipidation
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.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Synthesis of 20‐Membered Macrocyclic Pseudo‐Natural Products Yields Inducers of LC3 Lipidation ; day:25 ; month:01 ; year:2022 ; extent:1
Angewandte Chemie ; (25.01.2022) (gesamt 1)
- Urheber
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Niggemeyer, Georg
Knyazeva, Anastasia
Gasper, Raphael
Corkery, Dale
Bodenbinder, Pia
Holstein, Julian J.
Sievers, Sonja
Wu, Yao‐Wen
Waldmann, Herbert
- DOI
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10.1002/ange.202114328
- URN
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urn:nbn:de:101:1-2022012514234586976954
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:31 MESZ
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Beteiligte
- Niggemeyer, Georg
- Knyazeva, Anastasia
- Gasper, Raphael
- Corkery, Dale
- Bodenbinder, Pia
- Holstein, Julian J.
- Sievers, Sonja
- Wu, Yao‐Wen
- Waldmann, Herbert
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