ArticleNature chemistry2013
Simultaneous structure-activity studies and arming of natural products by C-H amination reveal cellular targets of eupalmerin acetate.
Article in Nature chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 38 papers.
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Who cites it
38 citing papers in PubMed, 122 citations in OpenAlex.
- Semisynthesis of Mycothiazole Analogs having Distinct Bioactivity.ACS medicinal chemistry letters · 2026Article
- Photoactive Iminobismuthanes for Catalytic C-H Amination.Journal of the American Chemical Society · 2026Article
- B(COrganic letters · 2026Article
- Chemical Tagging ofJournal of the American Chemical Society · 2025Article
- Copper-Catalyzed Allylic Amination of Alkenes UsingACS catalysis · 2025Article
- Improved deconvolution of natural products' protein targets using diagnostic ions from chemical proteomics linkers.Beilstein journal of organic chemistry · 2024Review
- Chemical Tagging of Bioactive Amides by Cooperative Catalysis: Applications in the Syntheses of Drug Conjugates.Journal of the American Chemical Society · 2023Article
- Transition-Metal-Catalyzed C-H Bond Activation for the Formation of C-C Bonds in Complex Molecules.Chemical reviews · 2023Review
- Aspartyl β-Turn-Based Dirhodium(II) Metallopeptides for Benzylic C(spJournal of the American Chemical Society · 2023Article
- Combining visible-light induction and copper catalysis for chemo-selective nitrene transfer for late-stage amination of natural products.Communications chemistry · 2022Article
- Stereoretentive and regioselective selenium-catalyzed intermolecular propargylic C-H amination of alkynes.Chemical science · 2022Article
- Late-Stage Intermolecular Allylic C-H Amination.Journal of the American Chemical Society · 2021Article
- Comprehensive Structure-Activity Profiling of Micheliolide and its Targeted Proteome in Leukemia Cells via Probe-Guided Late-Stage C-H Functionalization.ACS central science · 2021Article
- Nitrene-mediated intermolecular N-N coupling for efficient synthesis of hydrazides.Nature chemistry · 2021Article
- Currently Available Strategies for Target Identification of Bioactive Natural Products.Frontiers in chemistry · 2021Review
- Late-Stage Diversification of Natural Products.ACS central science · 2020Review
- Diversity-oriented synthesis of 17-spirosteroids.Beilstein journal of organic chemistry · 2020Article
- Sulfamyl Radicals Direct Photoredox-Mediated Giese Reactions at Unactivated C(3)-H Bonds.Organic letters · 2019Article
- Cobalt-based nanoparticles prepared from MOF-carbon templates as efficient hydrogenation catalysts.Chemical science · 2018Article
- Investigation of transition metal-catalyzed nitrene transfer reactions in water.Bioorganic & medicinal chemistry · 2018Article
Corrections and comments
- Erratum issued
Authors and funding
8 authors at 3 institutions in 2 countries.
Funding
Abstract
Natural products have a venerable history of, and enduring potential for the discovery of useful biological activity. To fully exploit this, the development of chemical methodology that can functionalize unique sites within these complex structures is highly desirable. Here, we describe the use of rhodium(II)-catalysed C-H amination reactions developed by Du Bois to carry out simultaneous structure-activity relationship studies and arming (alkynylation) of natural products at 'unfunctionalized' positions. Allylic and benzylic C-H bonds in the natural products undergo amination while olefins undergo aziridination, and tertiary amine-containing natural products are converted to amidines by a C-H amination-oxidation sequence or to hydrazine sulfamate zwitterions by an unusual N-amination. The alkynylated derivatives are ready for conversion into cellular probes that can be used for mechanism-of-action studies. Chemo- and site-selectivity was studied with a diverse library of natural products. For one of these-the marine-derived anticancer diterpene, eupalmerin acetate-quantitative proteome profiling led to the identification of several protein targets in HL-60 cells, suggesting a polypharmacological mode of action.
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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.