Literature DB >> 33479601

Structure-based design and analysis of SuFEx chemical probes.

Lyn H Jones1, Jeffery W Kelly2.   

Abstract

The discerning reactivity of sulfur(vi)-fluoride exchange (SuFEx) chemistry has enabled the context-specific labeling of protein binding sites by chemical probes that incorporate these versatile warheads. Emerging information from protein-probe structures and proteomic mapping experiments is helping advance our understanding of the protein microenvironment that dictates the reactivity of targetable amino acid residues. This review explores these new findings that should influence the future rational design of SuFEx probes for a multitude of applications in chemical biology and drug discovery. This journal is © The Royal Society of Chemistry 2020.

Entities:  

Year:  2020        PMID: 33479601      PMCID: PMC7460715          DOI: 10.1039/c9md00542k

Source DB:  PubMed          Journal:  RSC Med Chem        ISSN: 2632-8682


  53 in total

1.  Covalent Enzyme Inhibition through Fluorosulfate Modification of a Noncatalytic Serine Residue.

Authors:  Olugbeminiyi O Fadeyi; Lise R Hoth; Chulho Choi; Xidong Feng; Ariamala Gopalsamy; Erik C Hett; Robert E Kyne; Ralph P Robinson; Lyn H Jones
Journal:  ACS Chem Biol       Date:  2017-07-20       Impact factor: 5.100

2.  Aryl-fluorosulfate-based Lysine Covalent Pan-Inhibitors of Apoptosis Protein (IAP) Antagonists with Cellular Efficacy.

Authors:  Carlo Baggio; Parima Udompholkul; Luca Gambini; Ahmed F Salem; Jennifer Jossart; J Jefferson P Perry; Maurizio Pellecchia
Journal:  J Med Chem       Date:  2019-10-08       Impact factor: 7.446

3.  Structure of the Adenosine A1 Receptor Reveals the Basis for Subtype Selectivity.

Authors:  Alisa Glukhova; David M Thal; Anh T Nguyen; Elizabeth A Vecchio; Manuela Jörg; Peter J Scammells; Lauren T May; Patrick M Sexton; Arthur Christopoulos
Journal:  Cell       Date:  2017-02-23       Impact factor: 41.582

4.  Irreversible enzyme inhibitors. CXII. Active-site-directed irreversible inhibitors of dihydrofolic reductase derived from 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-phenyl-s-triazine substituted with a terminal sulfonyl fluoride. II.

Authors:  B R Baker; G J Lourens
Journal:  J Med Chem       Date:  1968-01       Impact factor: 7.446

Review 5.  Affinity labeling of purine nucleotide sites in proteins.

Authors:  R F Colman
Journal:  Annu Rev Biochem       Date:  1983       Impact factor: 23.643

6.  Direct evidence that oncogenic tyrosine kinases and cyclic AMP-dependent protein kinase have homologous ATP-binding sites.

Authors:  M P Kamps; S S Taylor; B M Sefton
Journal:  Nature       Date:  1984 Aug 16-22       Impact factor: 49.962

7.  A study of the reactivity of S(VI)-F containing warheads with nucleophilic amino-acid side chains under physiological conditions.

Authors:  H Mukherjee; J Debreczeni; J Breed; S Tentarelli; B Aquila; J E Dowling; A Whitty; N P Grimster
Journal:  Org Biomol Chem       Date:  2017-11-22       Impact factor: 3.876

8.  Covalent Allosteric Probe for the Metabotropic Glutamate Receptor 2: Design, Synthesis, and Pharmacological Characterization.

Authors:  Maarten L J Doornbos; Xuesong Wang; Sophie C Vermond; Luc Peeters; Laura Pérez-Benito; Andrés A Trabanco; Hilde Lavreysen; José María Cid; Laura H Heitman; Gary Tresadern; Adriaan P IJzerman
Journal:  J Med Chem       Date:  2018-03-07       Impact factor: 7.446

9.  Binding site elucidation and structure guided design of macrocyclic IL-17A antagonists.

Authors:  Shenping Liu; Leslie A Dakin; Li Xing; Jane M Withka; Parag V Sahasrabudhe; Wei Li; Mary Ellen Banker; Paul Balbo; Suman Shanker; Boris A Chrunyk; Zuojun Guo; Jinshan M Chen; Jennifer A Young; Guoyun Bai; Jeremy T Starr; Stephen W Wright; Joerg Bussenius; Sheng Tan; Ariamala Gopalsamy; Bruce A Lefker; Fabien Vincent; Lyn H Jones; Hua Xu; Lise R Hoth; Kieran F Geoghegan; Xiayang Qiu; Mark E Bunnage; Atli Thorarensen
Journal:  Sci Rep       Date:  2016-08-16       Impact factor: 4.379

10.  Structural Basis for Binding of Allosteric Drug Leads in the Adenosine A1 Receptor.

Authors:  Yinglong Miao; Apurba Bhattarai; Anh T N Nguyen; Arthur Christopoulos; Lauren T May
Journal:  Sci Rep       Date:  2018-11-15       Impact factor: 4.379

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  11 in total

Review 1.  Reactive chemistry for covalent probe and therapeutic development.

Authors:  R Justin Grams; Ku-Lung Hsu
Journal:  Trends Pharmacol Sci       Date:  2022-01-06       Impact factor: 14.819

2.  Calcium Bistriflimide-Mediated Sulfur(VI)-Fluoride Exchange (SuFEx): Mechanistic Insights toward Instigating Catalysis.

Authors:  Brian Han; Samuel R Khasnavis; Matthew Nwerem; Michael Bertagna; Nicholas D Ball; O Maduka Ogba
Journal:  Inorg Chem       Date:  2022-06-14       Impact factor: 5.436

3.  Covalent labeling of a chromatin reader domain using proximity-reactive cyclic peptides.

Authors:  Meng Yao Zhang; Hyunjun Yang; Gloria Ortiz; Michael J Trnka; Nektaria Petronikolou; Alma L Burlingame; William F DeGrado; Danica Galonić Fujimori
Journal:  Chem Sci       Date:  2022-05-12       Impact factor: 9.969

4.  Amino-oxetanes as amide isosteres by an alternative defluorosulfonylative coupling of sulfonyl fluorides.

Authors:  Juan J Rojas; Rosemary A Croft; Alistair J Sterling; Edward L Briggs; Daniele Antermite; Daniel C Schmitt; Luka Blagojevic; Peter Haycock; Andrew J P White; Fernanda Duarte; Chulho Choi; James J Mousseau; James A Bull
Journal:  Nat Chem       Date:  2022-01-27       Impact factor: 24.274

5.  Photoredox catalytic radical fluorosulfonylation of olefins enabled by a bench-stable redox-active fluorosulfonyl radical precursor.

Authors:  Peng Wang; Honghai Zhang; Xingliang Nie; Tianxiao Xu; Saihu Liao
Journal:  Nat Commun       Date:  2022-06-11       Impact factor: 17.694

6.  Sulfur [18F]Fluoride Exchange Click Chemistry Enabled Ultrafast Late-Stage Radiosynthesis.

Authors:  Qinheng Zheng; Hongtao Xu; Hua Wang; Wen-Ge Han Du; Nan Wang; Huan Xiong; Yuang Gu; Louis Noodleman; K Barry Sharpless; Guang Yang; Peng Wu
Journal:  J Am Chem Soc       Date:  2021-02-25       Impact factor: 15.419

Review 7.  Modular Approaches to Synthesize Activity- and Affinity-Based Chemical Probes.

Authors:  Antonie J van der Zouwen; Martin D Witte
Journal:  Front Chem       Date:  2021-04-15       Impact factor: 5.221

Review 8.  Flipping the Switch: Innovations in Inducible Probes for Protein Profiling.

Authors:  Sean M McKenna; Ellen M Fay; Joanna F McGouran
Journal:  ACS Chem Biol       Date:  2021-11-15       Impact factor: 5.100

9.  Introducing SuFNucs: Sulfamoyl-Fluoride-Functionalized Nucleosides That Undergo Sulfur Fluoride Exchange Reaction.

Authors:  Mikołaj Chrominski; Kamil Ziemkiewicz; Joanna Kowalska; Jacek Jemielity
Journal:  Org Lett       Date:  2022-06-30       Impact factor: 6.072

10.  Scalable, Chemoselective Nickel Electrocatalytic Sulfinylation of Aryl Halides with SO2.

Authors:  Terry Shing-Bong Lou; Yu Kawamata; Tamara Ewing; Guillermo A Correa-Otero; Michael R Collins; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-03       Impact factor: 16.823

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