Literature DB >> 29044843

Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes.

Sabrina Bernard1, Davide Audisio1, Margaux Riomet1, Sarah Bregant2, Antoine Sallustrau1, Lucie Plougastel1, Elodie Decuypere1, Sandra Gabillet1, Ramar Arun Kumar1, Jijy Elyian1, Minh Nguyet Trinh3, Oleksandr Koniev4, Alain Wagner3, Sergii Kolodych4, Frédéric Taran1.   

Abstract

We report the discovery of a new bioorthogonal click-and-release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target-fishing applications. This click-and-release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  bioorthogonal reactions; chemical biology; cleavage reactions; click chemistry; mesoionic compounds

Year:  2017        PMID： 29044843     DOI： 10.1002/anie.201708790

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Origins of halogen effects in bioorthogonal sydnone cycloadditions.

Authors:  Huimin Tao; Fang Liu; Ruxin Zeng; Zhuzhou Shao; Lufeng Zou; Yang Cao; Jennifer M Murphy; K N Houk; Yong Liang
Journal:  Chem Commun (Camb)       Date:  2018-05-15       Impact factor: 6.222

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.  Selective Engineering of Linkage-Specific α2,6-N-Linked Sialoproteins Using Sydnone-Modified Sialic Acid Bioorthogonal Reporters.

Authors:  Zoeisha S Chinoy; Clément Bodineau; Camille Favre; Kelley W Moremen; Raúl V Durán; Frédéric Friscourt
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-19       Impact factor: 15.336

4.  Conditional and Reversible Activation of Class A and B G Protein-Coupled Receptors Using Tethered Pharmacology.

Authors:  Tom Podewin; Julia Ast; Johannes Broichhagen; Nicholas H F Fine; Daniela Nasteska; Philipp Leippe; Manuel Gailer; Teresa Buenaventura; Nisha Kanda; Ben J Jones; Celine M'Kadmi; Jean-Louis Baneres; Jacky Marie; Alejandra Tomas; Dirk Trauner; Anja Hoffmann-Röder; David J Hodson
Journal:  ACS Cent Sci       Date:  2018-01-16       Impact factor: 14.553

Review 5.  Triazole-Modified Nucleic Acids for the Application in Bioorganic and Medicinal Chemistry.

Authors:  Dagmara Baraniak; Jerzy Boryski
Journal:  Biomedicines       Date:  2021-05-31

6.  Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics.

Authors:  Mark A R de Geus; Elmer Maurits; Alexi J C Sarris; Thomas Hansen; Max S Kloet; Kiki Kamphorst; Wolter Ten Hoeve; Marc S Robillard; Andrea Pannwitz; Sylvestre A Bonnet; Jeroen D C Codée; Dmitri V Filippov; Herman S Overkleeft; Sander I van Kasteren
Journal:  Chemistry       Date:  2020-06-03       Impact factor: 5.236

Review 7.  Bioorthogonal Ligations and Cleavages in Chemical Biology.

Authors:  Youshan Li; Hua Fu
Journal:  ChemistryOpen       Date:  2020-08-14       Impact factor: 2.911

8.  Isonitrile-responsive and bioorthogonally removable tetrazine protecting groups.

Authors:  Julian Tu; Dennis Svatunek; Saba Parvez; Hannah J Eckvahl; Minghao Xu; Randall T Peterson; K N Houk; Raphael M Franzini
Journal:  Chem Sci       Date:  2019-11-05       Impact factor: 9.825
  8 in total

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