5 Sulfur Fluoride Exchange (SuFEx)

2022 ◽  
Author(s):  
M.-C. Giel ◽  
C. J. Smedley ◽  
J. E. Moses
Keyword(s):  
Click Chemistry ◽  
Oxidation State ◽  
High Oxidation State ◽  
Sulfuryl Fluoride ◽  
Metal Free ◽  
Sulfur Fluoride ◽  
New Generation ◽  
Sulfonyl Fluoride ◽  
Absolute Reliability ◽  
Generation Technology

AbstractSulfur Fluoride Exchange (SuFEx) click chemistry is a new generation technology for creating stable molecular connections with absolute reliability under metal-free conditions. SuFEx builds upon the fundamental principles of click chemistry by exploiting a unique blend of stability and latent reactivity of high oxidation state sulfur fluoride [e.g., S(VI)] functionalities to forge stable covalent linkages at connective SuFEx hubs. In this review, we focus mainly on the SuFEx hubs, sulfuryl fluoride (SO2F2), thionyl tetrafluoride (SOF4), ethenesulfonyl fluoride (ESF), 1-bromoethene-1-sulfonyl fluoride (BESF) and, 2-substituted alkyne-1-sulfonyl fluorides (SASFs). We describe each connector’s unique reactivity and their application to SuFEx click chemistry.

scholarly journals SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase

2019 ◽  
Vol 116 (38) ◽  
pp. 18808-18814 ◽  
Author(s):  
Qinheng Zheng ◽  
Jordan L. Woehl ◽  
Seiya Kitamura ◽  
Diogo Santos-Martins ◽  
Christopher J. Smedley ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Serine Protease ◽  
Neutrophil Elastase ◽  
Human Neutrophil ◽  
Cathepsin G ◽  
Human Neutrophil Elastase ◽  
Biological Assays ◽  
Covalent Inhibitors ◽  
Sulfur Fluoride ◽  
New Generation

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 optimization of covalent inhibitors of human neutrophil elastase (hNE). Evaluation of our ever-growing collection of SuFExable compounds toward various biological assays unexpectedly revealed a selective and covalent hNE inhibitor: benzene-1,2-disulfonyl fluoride. Synthetic derivatization of the initial hit led to a more potent agent, 2-(fluorosulfonyl)phenyl fluorosulfate with IC50 0.24 μM and greater than 833-fold selectivity over the homologous neutrophil serine protease, cathepsin G. The optimized, yet simple benzenoid probe only modified active hNE and not its denatured form.

Physical and technological basics and new generation technology of radiation- modified polymer concrete

2015 ◽  
Vol 37 (0) ◽  
pp. 116-122
Author(s):  
T. V. Kovalinska ◽  
А. G. Zelinskyi ◽  
V. I. Sakhno ◽  
О. М. Fainleib ◽  
D. Yu. Kolesnik ◽  
...  
Keyword(s):  
Polymer Concrete ◽  
Modified Polymer ◽  
New Generation ◽  
Generation Technology

Click Chemistry Expedited Radiosynthesis: Sulfur [18F]fluoride Exchange of Aryl Fluorosulfates

2019 ◽  
Author(s):  
Qinheng Zheng ◽  
Hongtao Xu ◽  
Hua Wang ◽  
Wen-Ge Han Du ◽  
Nan Wang ◽  
...  
Keyword(s):  
Click Chemistry ◽  
High Performance ◽  
Isotopic Exchange ◽  
Tumor Imaging ◽  
Radiochemical Yield ◽  
Exchange Method ◽  
Molar Activity ◽  
Positron Emission ◽  
Sulfur Fluoride

The lack of simple, efficient [<sup>18</sup>F]fluorination processes and new target-specific organofluorine probes remains the major challenge of fluorine-18-based positron emission tomography (PET). We report here a fast isotopic exchange method for the radiosynthesis of aryl [<sup>18</sup>F]fluorosulfate based PET agents enabled by the emerging sulfur fluoride exchange (SuFEx) click chemistry. The method has been applied to the fully-automated <sup>18</sup>F-radiolabeling of twenty-five structurally diverse aryl fluorosulfates with excellent radiochemical yield (83–100%) and high molar activity (up to 281 GBq µmol<sup>–1</sup>) at room temperature in 30 seconds. The purification of radiotracers requires no time-consuming high-performance liquid chromatography (HPLC), but rather a simple cartridge filtration. The utility of aryl [<sup>18</sup>F]fluorosulfate is demonstrated by the <i>in vivo</i> tumor imaging by targeting poly(ADP-ribose) polymerase 1 (PARP1).

Bifluoride Ion Mediated SuFEx Trifluoromethylation of Sulfonyl Fluorides and Iminosulfur Oxydifluorides

2018 ◽  
Author(s):  
Christopher J. Smedley ◽  
Bing Gao ◽  
Suhua Li ◽  
Qinheng Zheng ◽  
Andrew Molino ◽  
...  
Keyword(s):  
Breast Cancer Cells ◽  
Catalytic Mechanism ◽  
Bioactive Molecules ◽  
Chromatographic Purification ◽  
Rapid Exchange ◽  
Nucleophilic Displacement ◽  
Sulfur Fluoride ◽  
Reactions With Nucleophiles ◽  
New Generation ◽  
Selection Of

Sulfur-Fluoride Exchange (SuFEx) is the new generation click chemistry transformation exploiting the unique properties of S-F bonds and their ability to undergo near-perfect reactions with nucleophiles. We report here the first SuFEx based protocol for the efficient synthesis of pharmaceutically important triflones and bis(trifluoromethyl)sulfur oxyimines from the corresponding sulfonyl fluorides and iminosulfur oxydifluorides, respectively. The new protocol involves the rapid exchange of the S-F bond with trifluoromethyltrimethylsilane (TMSCF<sub>3</sub>) upon activation with potassium bifluoride in anhydrous DMSO. The reaction tolerates a wide selection of substrates and proceeds under mild conditions without need for chromatographic purification. A tentative catalytic mechanism is proposed supported by DFT calculations, involving formation of the free trifluoromethyl anion followed by nucleophilic displacement of the S-F through a five-coordinate intermediate. The preparation of a benzothiazole derived bis(trifluoromethyl)sulfur oxyimine with cytotoxic selectivity for MCF7 breast cancer cells demonstrates the utility of this methodology for the late-stage functionalization of bioactive molecules.<br>

scholarly journals Chemoselective bioconjugation based on modular click chemistry with 4-halocoumarins and aryl sulfonates

RSC Advances ◽  
2021 ◽  
Vol 11 (31) ◽  
pp. 18960-18965
Author(s):  
F. Yushra Thanzeel ◽  
Christian Wolf
Keyword(s):  
Click Chemistry ◽  
Bond Formation ◽  
Metal Free

We report chemoselective and modular peptide bioconjugation using stoichiometric amounts of 4-halocoumarin and arylsulfonate agents that undergo metal-free C(sp2)-heteroatom bond formation at micromolar concentrations.

SuFEx: a metal-free click ligation for multivalent biomolecules

2017 ◽  
Vol 15 (7) ◽  
pp. 1549-1553 ◽  
Author(s):  
Alessandro Dondoni ◽  
Alberto Marra
Keyword(s):  
Bovine Serum Albumin ◽  
Serum Albumin ◽  
Bovine Serum ◽  
Metal Free ◽  
Sulfonyl Fluoride

Sulfonamide-linked glycoclusters and sulfamate-linked BSA-PEG were prepared by coupling a sugar sulfonyl fluoride with a calixarene tetra-amine and a PEG-fluorosulfate with native bovine serum albumin, respectively.

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