Synthetic Matching of Complex Monoterpene Indole Alkaloid Chemical Space
Abstract: Monoterpene indole alkaloids (MIAs) are endowed with high structural and spatial complexity and characterized by diverse biological activities. Given this complexity‐activity combination in MIAs, rapid and efficient access to chemical matter related to and with complexity similar to these alkaloids would be highly desirable, since such compound classes might display novel bioactivity. We describe the design and synthesis of a pseudo‐natural product (pseudo‐NP) collection obtained by the unprecedented combination of MIA fragments through complexity‐generating transformations, resulting in arrangements not currently accessible by biosynthetic pathways. Cheminformatic analyses revealed that both the pseudo‐NPs and the MIAs reside in a unique and common area of chemical space with high spatial complexity‐density that is only sparsely populated by other natural products and drugs. Investigation of bioactivity guided by morphological profiling identified pseudo‐NPs that inhibit DNA synthesis and modulate tubulin. These results demonstrate that the pseudo‐NP collection occupies similar biologically relevant chemical space that Nature has endowed MIAs with.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Synthetic Matching of Complex Monoterpene Indole Alkaloid Chemical Space ; day:24 ; month:10 ; year:2023 ; extent:13
Angewandte Chemie / International edition. International edition ; (24.10.2023) (gesamt 13)
- Creator
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Xie, Jianing
Pahl, Axel
Krzyzanowski, Adrian
Krupp, Anna
Liu, Jie
Koska, Sandra
Schölermann, Beate
Zhang, Ruirui
Bonowski, Jana
Sievers, Sonja
Strohmann, Carsten
Ziegler, Slava
Grigalunas, Michael
Waldmann, Herbert
- DOI
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10.1002/anie.202310222
- URN
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urn:nbn:de:101:1-2023102515053180641955
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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2025-08-14T10:44:51+0200
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Xie, Jianing
- Pahl, Axel
- Krzyzanowski, Adrian
- Krupp, Anna
- Liu, Jie
- Koska, Sandra
- Schölermann, Beate
- Zhang, Ruirui
- Bonowski, Jana
- Sievers, Sonja
- Strohmann, Carsten
- Ziegler, Slava
- Grigalunas, Michael
- Waldmann, Herbert
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Tierexperimentelle Untersuchungen zum Einfluss von Fluconazol auf Parameter des humoralen und zellulären Immunsystems der Maus : Anwendung der Durchflusszytometrie- und ELISA-Technik
Monoterpene indole alkaloids with anticancer activity from Tabernaemontana species
Research on dynamic time warping multivariate time series similarity matching based on shape feature and inclination angle
Classical trajectory perspective of atomic ionization in strong laser fields : semiclassical modeling
Enhanced prediction of bolt support drilling pressure using optimized Gaussian process regression
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Efficient Palladium‐Catalyzed Aerobic Oxidative Carbocyclization to Seven‐Membered Heterocycles
Payment Clearing and Regional Economy Development Based on Panel Data of Sichuan Province
Middle Terms of AR-sequences of Graded Kronecker Modules
Reconstitution of monoterpene indole alkaloid biosynthesis in genome engineered Nicotiana benthamiana
Biosynthesis of natural and halogenated plant monoterpene indole alkaloids in yeast
Synthetic Matching of Complex Monoterpene Indole Alkaloid Chemical Space
Tierexperimentelle Untersuchungen zum Einfluss von Fluconazol auf Parameter des humoralen und zellulären Immunsystems der Maus : Anwendung der Durchflusszytometrie- und ELISA-Technik
Monoterpene indole alkaloids with anticancer activity from Tabernaemontana species
Research on dynamic time warping multivariate time series similarity matching based on shape feature and inclination angle
Classical trajectory perspective of atomic ionization in strong laser fields : semiclassical modeling
Enhanced prediction of bolt support drilling pressure using optimized Gaussian process regression
Meaning-oriented understanding of L2 academic writing development with task-type repetition
Efficient Palladium‐Catalyzed Aerobic Oxidative Carbocyclization to Seven‐Membered Heterocycles
Payment Clearing and Regional Economy Development Based on Panel Data of Sichuan Province
Middle Terms of AR-sequences of Graded Kronecker Modules
Reconstitution of monoterpene indole alkaloid biosynthesis in genome engineered Nicotiana benthamiana