Search Results - "Sharpless, K. Barry"
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Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry
Published in Angewandte Chemie International Edition (01-09-2014)“…Aryl sulfonyl chlorides (e.g. Ts‐Cl) are beloved of organic chemists as the most commonly used SVI electrophiles, and the parent sulfuryl chloride, O2SVICl2,…”
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SuFEx Click Chemistry Enabled Late-Stage Drug Functionalization
Published in Journal of the American Chemical Society (28-02-2018)“…Sulfur(VI) Fluoride Exchange (SuFEx) is a new family of click chemistry transformations which relies on readily available materials to produce compounds…”
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SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase
Published in Proceedings of the National Academy of Sciences - PNAS (17-09-2019)“…Sulfur fluoride exchange (SuFEx) has emerged as the new generation of click chemistry. We report here a SuFEx-enabled, agnostic approach for the discovery and…”
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A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an “F−SO2+” Donor of Unprecedented Reactivity, Selectivity, and Scope
Published in Angewandte Chemie International Edition (01-03-2018)“…Sulfuryl fluoride, SO2F2, has been found to derivatize phenols in all kinds of environments, even those in highly functional molecules. We now report that a…”
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SuFExable polymers with helical structures derived from thionyl tetrafluoride
Published in Nature chemistry (01-09-2021)“…Sulfur( vi ) fluoride exchange (SuFEx) is a category of click chemistry that enables covalent linking of modular units through sulfur( vi ) connective hubs…”
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Using sulfuramidimidoyl fluorides that undergo sulfur(vi) fluoride exchange for inverse drug discovery
Published in Nature chemistry (01-10-2020)“…Drug candidates that form covalent linkages with their target proteins have been underexplored compared with the conventional counterparts that modulate…”
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Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF4)‐Derived Connective Hubs for Bioconjugation to DNA and Proteins
Published in Angewandte Chemie International Edition (11-06-2019)“…We report here the development of a suite of biocompatible SuFEx transformations from the SOF4‐derived iminosulfur oxydifluoride hub in aqueous buffer…”
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SuFEx‐Based Polysulfonate Formation from Ethenesulfonyl Fluoride–Amine Adducts
Published in Angewandte Chemie (International ed.) (04-09-2017)“…The SuFEx‐based polycondensation between bisalkylsulfonyl fluorides (AA monomers) and bisphenol bis(t‐butyldimethylsilyl) ethers (BB monomers) using…”
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Copper(I)‐Catalyzed Cycloaddition of Organic Azides and 1‐Iodoalkynes
Published in Angewandte Chemie International Edition (01-01-2009)“…High fidelity: 1‐Iodoalkynes react rapidly and selectively with organic azides in the presence of copper(I) catalysts (see scheme;…”
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Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2‐Substituted‐Alkynyl‐1‐Sulfonyl Fluoride (SASF) Hubs
Published in Angewandte Chemie International Edition (20-07-2020)“…Diversity Oriented Clicking (DOC) is a unified click‐approach for the modular synthesis of lead‐like structures through application of the wide family of click…”
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Bacterial glycosyltransferase-mediated cell-surface chemoenzymatic glycan modification
Published in Nature communications (17-04-2019)“…Chemoenzymatic modification of cell-surface glycan structures has emerged as a complementary approach to metabolic oligosaccharide engineering. Here, we…”
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Pharmacology, Pharmacokinetics, and Tissue Disposition of Zwitterionic Hydroxyiminoacetamido Alkylamines as Reactivating Antidotes for Organophosphate Exposure
Published in The Journal of pharmacology and experimental therapeutics (01-11-2018)“…In the development of antidotal therapy for treatment of organophosphate exposure from pesticides used in agriculture and nerve agents insidiously employed in…”
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SuFEx-based chemical diversification for the systematic discovery of CRBN molecular glues
Published in Bioorganic & medicinal chemistry (15-04-2024)“…[Display omitted] Molecular glues are small molecules that stabilize protein–protein interactions, enabling new molecular pharmacologies, such as targeted…”
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Copper-Catalyzed Synthesis of N-Sulfonyl-1,2,3-triazoles: Controlling Selectivity
Published in Angewandte Chemie International Edition (01-01-2007)“…4‐Substituted 1‐(N‐sulfonyl)‐1,2,3‐triazoles are selectively obtained by using the Cu‐catalyzed azide–alkyne cycloaddition reaction with sulfonyl azides…”
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Efficient Synthesis of 2-Substituted-1,2,3-triazoles
Published in Organic letters (07-08-2008)“…In this three-component reaction, alkynes undergo a copper(I)-catalyzed cycloaddition with sodium azide and formaldehyde to yield…”
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Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates
Published in Journal of the American Chemical Society (12-01-2005)“…Huisgen's 1,3-dipolar cycloadditions become nonconcerted when copper(I) acetylides react with azides and nitrile oxides, providing ready access to…”
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Quantitative and Orthogonal Formation and Reactivity of SuFEx Platforms
Published in Chemistry : a European journal (20-07-2018)“…The constraints of minute reactant amounts and the impossibility to remove any undesired surface‐bound products during monolayer functionalization of a surface…”
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A Fluorogenic Aryl Fluorosulfate for Intraorganellar Transthyretin Imaging in Living Cells and in Caenorhabditis elegans
Published in Journal of the American Chemical Society (17-06-2015)“…Fluorogenic probes, due to their often greater spatial and temporal sensitivity in comparison to permanently fluorescent small molecules, represent powerful…”
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A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes
Published in Angewandte Chemie International Edition (15-07-2002)“…By simply stirring in water, organic azides and terminal alkynes are readily and cleanly converted into 1,4‐disubstituted 1,2,3‐triazoles through a highly…”
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Ruthenium-Catalyzed Cycloaddition of Alkynes and Organic Azides
Published in Journal of the American Chemical Society (23-11-2005)“…Cp*RuCl(PPh3)2 is an effective catalyst for the regioselective “fusion” of organic azides and terminal alkynes, producing 1,5-disubstituted 1,2,3-triazoles…”
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