Literature DB >> 20865197

Azirine ligation: fast and selective protein conjugation via photoinduced azirine-alkene cycloaddition.

Reyna K V Lim1, Qing Lin.   

Abstract

We report a new bioorthogonal ligation reaction between p-nitrodiphenylazirine and dimethyl fumarate. This photoinduced azirine-alkene cycloaddition provides a rapid (~2 min) and highly selective route to protein conjugation at neutral pH and room temperature in biological medium.

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Year:  2010        PMID： 20865197      PMCID： PMC2964347          DOI： 10.1039/c0cc02863k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  15 in total

Review 1.  Bioorthogonal chemistry: recent progress and future directions.

Authors:  Reyna K V Lim; Qing Lin
Journal:  Chem Commun (Camb)       Date:  2010-01-21       Impact factor: 6.222

2.  Ligand-directed tosyl chemistry for protein labeling in vivo.

Authors:  Shinya Tsukiji; Masayoshi Miyagawa; Yousuke Takaoka; Tomonori Tamura; Itaru Hamachi
Journal:  Nat Chem Biol       Date:  2009-03-29       Impact factor: 15.040

3.  A bioorthogonal chemistry strategy for probing protein lipidation in live cells.

Authors:  Wenjiao Song; Zhipeng Yu; Michael M Madden; Qing Lin
Journal:  Mol Biosyst       Date:  2010-04-30

4.  A metabolic alkene reporter for spatiotemporally controlled imaging of newly synthesized proteins in Mammalian cells.

Authors:  Wenjiao Song; Yizhong Wang; Zhipeng Yu; Claudia I Rivera Vera; Jun Qu; Qing Lin
Journal:  ACS Chem Biol       Date:  2010-09-17       Impact factor: 5.100

Review 5.  Cell signaling in space and time: where proteins come together and when they're apart.

Authors:  John D Scott; Tony Pawson
Journal:  Science       Date:  2009-11-27       Impact factor: 47.728

Review 6.  Why and how bacteria localize proteins.

Authors:  L Shapiro; H H McAdams; R Losick
Journal:  Science       Date:  2009-11-27       Impact factor: 47.728

7.  Nitrile ylide dimerization: investigation of the carbene reactivity of nitrile ylides.

Authors:  Suzanne Fergus; Stephen J Eustace; Anthony F Hegarty
Journal:  J Org Chem       Date:  2004-07-09       Impact factor: 4.354

8.  Large-scale profiling of protein palmitoylation in mammalian cells.

Authors:  Brent R Martin; Benjamin F Cravatt
Journal:  Nat Methods       Date:  2009-01-11       Impact factor: 28.547

9.  Bioorthogonal chemistry: fishing for selectivity in a sea of functionality.

Authors:  Ellen M Sletten; Carolyn R Bertozzi
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  In vivo imaging of membrane-associated glycans in developing zebrafish.

Authors:  Scott T Laughlin; Jeremy M Baskin; Sharon L Amacher; Carolyn R Bertozzi
Journal:  Science       Date:  2008-05-02       Impact factor: 47.728
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  15 in total

Review 1.  Photo-Triggered Click Chemistry for Biological Applications.

Authors:  András Herner; Qing Lin
Journal:  Top Curr Chem (Cham)       Date:  2015-12-11

2.  Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction.

Authors:  Peng An; Zhipeng Yu; Qing Lin
Journal:  Org Lett       Date:  2013-10-10       Impact factor: 6.005

Review 3.  Click chemistry in complex mixtures: bioorthogonal bioconjugation.

Authors:  Craig S McKay; M G Finn
Journal:  Chem Biol       Date:  2014-09-18

4.  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

Review 5.  Photoinducible bioorthogonal chemistry: a spatiotemporally controllable tool to visualize and perturb proteins in live cells.

Authors:  Reyna K V Lim; Qing Lin
Journal:  Acc Chem Res       Date:  2011-05-20       Impact factor: 22.384

6.  Design and synthesis of highly reactive dienophiles for the tetrazine-trans-cyclooctene ligation.

Authors:  Michael T Taylor; Melissa L Blackman; Olga Dmitrenko; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2011-06-06       Impact factor: 15.419

7.  Copper-free Sonogashira cross-coupling for functionalization of alkyne-encoded proteins in aqueous medium and in bacterial cells.

Authors:  Nan Li; Reyna K V Lim; Selvakumar Edwardraja; Qing Lin
Journal:  J Am Chem Soc       Date:  2011-09-13       Impact factor: 15.419

8.  Seeking Citius: Photochemical Access of Reactive Intermediates for Faster Bioorthogonal Reactions.

Authors:  Gangam Srikanth Kumar; Qing Lin
Journal:  Chembiochem       Date:  2022-06-09       Impact factor: 3.461

Review 9.  Photo-controllable bioorthogonal chemistry for spatiotemporal control of bio-targets in living systems.

Authors:  Jinbo Li; Hao Kong; Chenghong Zhu; Yan Zhang
Journal:  Chem Sci       Date:  2020-03-10       Impact factor: 9.825

10.  Enabling In Vivo Photocatalytic Activation of Rapid Bioorthogonal Chemistry by Repurposing Silicon-Rhodamine Fluorophores as Cytocompatible Far-Red Photocatalysts.

Authors:  Chuanqi Wang; He Zhang; Tao Zhang; Xiaoyu Zou; Hui Wang; Julia E Rosenberger; Raghu Vannam; William S Trout; Jonathan B Grimm; Luke D Lavis; Colin Thorpe; Xinqiao Jia; Zibo Li; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2021-07-12       Impact factor: 16.383
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