Literature DB >> 30034581

Emerging Utility of Fluorosulfate Chemical Probes.

Lyn H Jones1.   

Abstract

Aryl fluorosulfates are finding widespread utility in chemical biology and medicinal chemistry. The context-dependent engagement of tyrosine, lysine, serine, and histidine amino acid residues in functional protein sites has enabled chemogenomic and chemoproteomic techniques that demonstrate considerable promise for drug discovery and biomedical research.

Entities:  

Year:  2018        PMID： 30034581      PMCID： PMC6047027          DOI： 10.1021/acsmedchemlett.8b00276

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  12 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.  A New Portal to SuFEx Click Chemistry: A Stable Fluorosulfuryl Imidazolium Salt Emerging as an "F-SO2 +" Donor of Unprecedented Reactivity, Selectivity, and Scope.

Authors:  Taijie Guo; Genyi Meng; Xiongjie Zhan; Qian Yang; Tiancheng Ma; Long Xu; K Barry Sharpless; Jiajia Dong
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-25       Impact factor: 15.336

3.  Sulfur(VI) fluoride exchange (SuFEx): another good reaction for click chemistry.

Authors:  Jiajia Dong; Larissa Krasnova; M G Finn; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-11       Impact factor: 15.336

4.  Introduction of a Crystalline, Shelf-Stable Reagent for the Synthesis of Sulfur(VI) Fluorides.

Authors:  Hua Zhou; Paramita Mukherjee; Rongqiang Liu; Edelweiss Evrard; Dianpeng Wang; John M Humphrey; Todd W Butler; Lise R Hoth; Jeffrey B Sperry; Sylvie K Sakata; Christopher J Helal; Christopher W Am Ende
Journal:  Org Lett       Date:  2018-01-12       Impact factor: 6.005

5.  "Inverse Drug Discovery" Strategy To Identify Proteins That Are Targeted by Latent Electrophiles As Exemplified by Aryl Fluorosulfates.

Authors:  David E Mortenson; Gabriel J Brighty; Lars Plate; Grant Bare; Wentao Chen; Suhua Li; Hua Wang; Benjamin F Cravatt; Stefano Forli; Evan T Powers; K Barry Sharpless; Ian A Wilson; Jeffery W Kelly
Journal:  J Am Chem Soc       Date:  2017-12-21       Impact factor: 15.419

6.  Arylfluorosulfates Inactivate Intracellular Lipid Binding Protein(s) through Chemoselective SuFEx Reaction with a Binding Site Tyr Residue.

Authors:  Wentao Chen; Jiajia Dong; Lars Plate; David E Mortenson; Gabriel J Brighty; Suhua Li; Yu Liu; Andrea Galmozzi; Peter S Lee; Jonathan J Hulce; Benjamin F Cravatt; Enrique Saez; Evan T Powers; Ian A Wilson; K Barry Sharpless; Jeffery W Kelly
Journal:  J Am Chem Soc       Date:  2016-06-02       Impact factor: 15.419

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.  A fluorogenic aryl fluorosulfate for intraorganellar transthyretin imaging in living cells and in Caenorhabditis elegans.

Authors:  Aleksandra Baranczak; Yu Liu; Stephen Connelly; Wen-Ge Han Du; Erin R Greiner; Joseph C Genereux; R Luke Wiseman; Yvonne S Eisele; Nadine C Bradbury; Jiajia Dong; Louis Noodleman; K Barry Sharpless; Ian A Wilson; Sandra E Encalada; Jeffery W Kelly
Journal:  J Am Chem Soc       Date:  2015-06-08       Impact factor: 15.419

9.  Genetically Encoding Fluorosulfate-l-tyrosine To React with Lysine, Histidine, and Tyrosine via SuFEx in Proteins in Vivo.

Authors:  Nanxi Wang; Bing Yang; Caiyun Fu; He Zhu; Feng Zheng; Tomonori Kobayashi; Jun Liu; Shanshan Li; Cheng Ma; Peng G Wang; Qian Wang; Lei Wang
Journal:  J Am Chem Soc       Date:  2018-04-05       Impact factor: 15.419

10.  Sulfonyl fluorides as privileged warheads in chemical biology.

Authors:  Arjun Narayanan; Lyn H Jones
Journal:  Chem Sci       Date:  2015-03-16       Impact factor: 9.825
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  14 in total

Review 1.  Structure-based design and analysis of SuFEx chemical probes.

Authors:  Lyn H Jones; Jeffery W Kelly
Journal:  RSC Med Chem       Date:  2020-01-06

2.  Bioorthogonal chemistry.

Authors:  Samuel L Scinto; Didier A Bilodeau; Robert Hincapie; Wankyu Lee; Sean S Nguyen; Minghao Xu; Christopher W Am Ende; M G Finn; Kathrin Lang; Qing Lin; John Paul Pezacki; Jennifer A Prescher; Marc S Robillard; Joseph M Fox
Journal:  Nat Rev Methods Primers       Date:  2021-04-15

3.  Diversity oriented clicking delivers β-substituted alkenyl sulfonyl fluorides as covalent human neutrophil elastase inhibitors.

Authors:  Yunfei Cheng; Gencheng Li; Christopher J Smedley; Marie-Claire Giel; Seiya Kitamura; Jordan L Woehl; Giulia Bianco; Stefano Forli; Joshua A Homer; John R Cappiello; Dennis W Wolan; John E Moses; K Barry Sharpless
Journal:  Proc Natl Acad Sci U S A       Date:  2022-09-07       Impact factor: 12.779

4.  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

5.  A practical fluorosulfonylating platform via photocatalytic imidazolium-based SO2F radical reagent.

Authors:  Weigang Zhang; Heyin Li; Xiaojuan Li; Zhenlei Zou; Mengjun Huang; Jiyang Liu; Xiaochen Wang; Shengyang Ni; Yi Pan; Yi Wang
Journal:  Nat Commun       Date:  2022-06-18       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

7.  Covalent Inhibition of Wild-Type HIV-1 Reverse Transcriptase Using a Fluorosulfate Warhead.

Authors:  Joseph A Ippolito; Haichan Niu; Nicole Bertoletti; Zachary J Carter; Shengyan Jin; Krasimir A Spasov; José A Cisneros; Margarita Valhondo; Kara J Cutrona; Karen S Anderson; William L Jorgensen
Journal:  ACS Med Chem Lett       Date:  2021-01-06       Impact factor: 4.345

Review 8.  Arylfluorosulfate-Based Electrophiles for Covalent Protein Labeling: A New Addition to the Arsenal.

Authors:  Pablo Martín-Gago; Christian A Olsen
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-26       Impact factor: 15.336

9.  Photoredox-catalyzed aminofluorosulfonylation of unactivated olefins.

Authors:  Tao Zhong; Ji-Tao Yi; Zhi-Da Chen; Quan-Can Zhuang; Yong-Zhao Li; Gui Lu; Jiang Weng
Journal:  Chem Sci       Date:  2021-06-07       Impact factor: 9.825

10.  A Genetically Encoded Fluorosulfonyloxybenzoyl-l-lysine for Expansive Covalent Bonding of Proteins via SuFEx Chemistry.

Authors:  Jun Liu; Li Cao; Paul C Klauser; Rujin Cheng; Viktoriya Y Berdan; Wei Sun; Nanxi Wang; Farid Ghelichkhani; Bingchen Yu; Sharon Rozovsky; Lei Wang
Journal:  J Am Chem Soc       Date:  2021-07-02       Impact factor: 16.383
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