Literature DB >> 28332844

Aryl Fluorosulfate Trapped Staudinger Reduction.

Gerui Ren1, Qinheng Zheng, Hua Wang.   

Abstract

A chemoselective Staudinger reduction/sulfur(VI) fluoride exchange cascade has been developn>ed to join two chemical segments through an aryl sulfamate ester (RNH-SO2-OAr) linkage. Aryl fluorosulfate is exploited in this work as the first tetrahedral electrophilic trap for the in situ generated iminophosphorane. Ten examples using azide-containing compounds are presented.

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Year:  2017        PMID： 28332844      PMCID： PMC5922792          DOI： 10.1021/acs.orglett.7b00406

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  15 in total

Review 1.  The Staudinger ligation-a gift to chemical biology.

Authors:  Maja Köhn; Rolf Breinbauer
Journal:  Angew Chem Int Ed Engl       Date:  2004-06-14       Impact factor: 15.336

2.  Mechanistic investigation of the staudinger ligation.

Authors:  Fiona L Lin; Helen M Hoyt; Herman van Halbeek; Robert G Bergman; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2005-03-02       Impact factor: 15.419

3.  Towards quorum-quenching catalytic antibodies.

Authors:  Prashant B Kapadnis; Evan Hall; Madeleine Ramstedt; Warren R J D Galloway; Martin Welch; David R Spring
Journal:  Chem Commun (Camb)       Date:  2008-12-11       Impact factor: 6.222

Review 4.  Bioconjugation via azide-Staudinger ligation: an overview.

Authors:  Christine I Schilling; Nicole Jung; Moritz Biskup; Ute Schepers; Stefan Bräse
Journal:  Chem Soc Rev       Date:  2011-06-17       Impact factor: 54.564

Review 5.  Staudinger ligation as a method for bioconjugation.

Authors:  Sander S van Berkel; Mark B van Eldijk; Jan C M van Hest
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-02       Impact factor: 15.336

6.  Reengineering Antibiotics to Combat Bacterial Resistance: Click Chemistry [1,2,3]-Triazole Vancomycin Dimers with Potent Activity against MRSA and VRE.

Authors:  Steven M Silverman; John E Moses; K Barry Sharpless
Journal:  Chemistry       Date:  2016-11-11       Impact factor: 5.236

7.  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

8.  Matrix-assisted polymer pen lithography induced Staudinger Ligation.

Authors:  Shudan Bian; Kevin B Schesing; Adam B Braunschweig
Journal:  Chem Commun (Camb)       Date:  2012-04-16       Impact factor: 6.222

9.  Cell surface engineering by a modified Staudinger reaction.

Authors:  E Saxon; C R Bertozzi
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

10.  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
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  5 in total

1.  SuFEx Chemistry of Thionyl Tetrafluoride (SOF4 ) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates.

Authors:  Bing Gao; Suhua Li; Peng Wu; John E Moses; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-16       Impact factor: 15.336

2.  Developing bioorthogonal probes to span a spectrum of reactivities.

Authors:  Sean S Nguyen; Jennifer A Prescher
Journal:  Nat Rev Chem       Date:  2020-07-21       Impact factor: 34.035

3.  SuFEx-enabled, agnostic discovery of covalent inhibitors of human neutrophil elastase.

Authors:  Qinheng Zheng; Jordan L Woehl; Seiya Kitamura; Diogo Santos-Martins; Christopher J Smedley; Gencheng Li; Stefano Forli; John E Moses; Dennis W Wolan; K Barry Sharpless
Journal:  Proc Natl Acad Sci U S A       Date:  2019-09-04       Impact factor: 11.205

4.  Biocompatible SuFEx Click Chemistry: Thionyl Tetrafluoride (SOF4 )-Derived Connective Hubs for Bioconjugation to DNA and Proteins.

Authors:  Feng Liu; Hua Wang; Suhua Li; Grant A L Bare; Xuemin Chen; Chu Wang; John E Moses; Peng Wu; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2019-05-08       Impact factor: 15.336

5.  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
  5 in total

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