ArticleNature chemistry2012
Electronic tuning of site-selectivity.
Article in Nature chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
25 citing papers in PubMed, 55 citations in OpenAlex.
- Rapid prediction of conformationally-dependent DFT-level descriptors using graph neural networks for carboxylic acids and alkyl amines.Digital discovery · 2025Article
- Carbene-catalyzed chirality-controlled site-selective acylation of saccharides.Nature communications · 2025Article
- Tailored chiral phosphoramidites support highly enantioselective Pd catalysts for asymmetric aminoalkylative amination.Nature communications · 2024Article
- Palladium-catalyzed cross-coupling of alcohols with olefins by positional tuning of a counteranion.Science (New York, N.Y.) · 2024Article
- Site-selective chemical reactions by on-water surface sequential assembly.Nature communications · 2023Article
- Controlling the Site Selectivity in Acylations of Amphiphilic Diols: Directing the Reaction toward the Apolar Domain in a Model Diol and the Midecamycin AThe Journal of organic chemistry · 2022Article
- Site-switchable mono-O-allylation of polyols.Nature communications · 2020Article
- Synergistic photoredox and copper catalysis by diode-like coordination polymer with twisted and polar copper-dye conjugation.Nature communications · 2020Article
- Fixing the Unfixable: The Art of Optimizing Natural Products for Human Medicine.Journal of medicinal chemistry · 2019Review
- Site-Selective Switching Strategies to Functionalize Polyazines.Journal of the American Chemical Society · 2018Article
- Late-stage chemoselective functional-group manipulation of bioactive natural products with super-electrophilic silylium ions.Nature chemistry · 2018Article
- Highly selective acylation of polyamines and aminoglycosides by 5-acyl-5-phenyl-1,5-dihydro-4Chemical science · 2017Article
- Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.Chemical reviews · 2017Review
- Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis.Accounts of chemical research · 2017Article
- Π-Clamp-mediated cysteine conjugation.Nature chemistry · 2016Article
- Structure diversification of vancomycin through peptide-catalyzed, site-selective lipidation: a catalysis-based approach to combat glycopeptide-resistant pathogens.Journal of medicinal chemistry · 2015Article
- Macrocycles: lessons from the distant past, recent developments, and future directions.Chemical science · 2015Article
- Recent progress in the study of the interactions of amphotericin B with cholesterol and ergosterol in lipid environments.European biophysics journal : EBJ · 2014Review
- X-ray crystal structure of teicoplanin A₂-2 bound to a catalytic peptide sequence via the carrier protein strategy.The Journal of organic chemistry · 2014Article
- Chemo- and site-selective derivatizations of natural products enabling biological studies.Natural product reports · 2014Review
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6 authors at 2 institutions in 1 country.
Funding
Abstract
Site-selective functionalizations of complex small molecules can generate targeted derivatives with exceptional step efficiency, but general strategies for maximizing selectivity in this context are rare. Here, we report that site-selectivity can be tuned by simply modifying the electronic nature of the reagents. A Hammett analysis is consistent with linking this phenomenon to the Hammond postulate: electronic tuning to a more product-like transition state amplifies site-discriminating interactions between a reagent and its substrate. This strategy transformed a minimally site-selective acylation reaction into a highly selective and thus preparatively useful one. Electronic tuning of both an acylpyridinium donor and its carboxylate counterion further promoted site-divergent functionalizations. With these advances, we achieve a range of modifications to just one of the many hydroxyl groups appended to the ion channel-forming natural product amphotericin B. Thus, electronic tuning of reagents represents an effective strategy for discovering and optimizing site-selective functionalization reactions.
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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.