Literature DB >> 19544336

Fast alkene functionalization in vivo by Photoclick chemistry: HOMO lifting of nitrile imine dipoles.

Yizhong Wang1, Wenjiao Song, Wen J Hu, Qing Lin.   

Abstract

Extremely fast fluorescence labeling (<1 min) of a recombinant alkene-encoded protein in living Escherichia coli cells was observed with tetrazole 1. The electron-donating methoxy substituent raises the energy of the highest occupied molecular orbital of the nitrile-imine intermediate derived from 1. This strategy greatly accelerates the functionalization of alkenes by 1,3-dipolar cycloaddition in living systems.

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Year:  2009        PMID： 19544336      PMCID： PMC2763439          DOI： 10.1002/anie.200901220

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


  15 in total

1.  A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.

Authors:  Vsevolod V Rostovtsev; Luke G Green; Valery V Fokin; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2002-07-15       Impact factor: 15.336

Review 2.  Activity-based protein profiling for the functional annotation of enzymes.

Authors:  Katherine T Barglow; Benjamin F Cravatt
Journal:  Nat Methods       Date:  2007-10       Impact factor: 28.547

3.  Selective functionalization of a genetically encoded alkene-containing protein via "photoclick chemistry" in bacterial cells.

Authors:  Wenjiao Song; Yizhong Wang; Jun Qu; Qing Lin
Journal:  J Am Chem Soc       Date:  2008-07-02       Impact factor: 15.419

4.  Site-specific PEGylation of proteins containing unnatural amino acids.

Authors:  Alexander Deiters; T Ashton Cropp; Daniel Summerer; Mridul Mukherji; Peter G Schultz
Journal:  Bioorg Med Chem Lett       Date:  2004-12-06       Impact factor: 2.823

5.  Cell surface engineering by a modified Staudinger reaction.

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

6.  The ubiquitin ligase COP1 is a critical negative regulator of p53.

Authors:  David Dornan; Ingrid Wertz; Harumi Shimizu; David Arnott; Gretchen D Frantz; Patrick Dowd; Karen O'Rourke; Hartmut Koeppen; Vishva M Dixit
Journal:  Nature       Date:  2004-04-21       Impact factor: 49.962

7.  Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity.

Authors:  Melissa L Blackman; Maksim Royzen; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2008-09-18       Impact factor: 15.419

8.  Copper-free click chemistry for dynamic in vivo imaging.

Authors:  Jeremy M Baskin; Jennifer A Prescher; Scott T Laughlin; Nicholas J Agard; Pamela V Chang; Isaac A Miller; Anderson Lo; Julian A Codelli; Carolyn R Bertozzi
Journal:  Proc Natl Acad Sci U S A       Date:  2007-10-17       Impact factor: 11.205

9.  Convenient synthesis of highly functionalized pyrazolines via mild, photoactivated 1,3-dipolar cycloaddition.

Authors:  Yizhong Wang; Claudia I Rivera Vera; Qing Lin
Journal:  Org Lett       Date:  2007-09-15       Impact factor: 6.005

10.  A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems.

Authors:  Nicholas J Agard; Jennifer A Prescher; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419
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  51 in total

Review 1.  Designer proteins: applications of genetic code expansion in cell biology.

Authors:  Lloyd Davis; Jason W Chin
Journal:  Nat Rev Mol Cell Biol       Date:  2012-02-15       Impact factor: 94.444

Review 2.  Photo-Triggered Click Chemistry for Biological Applications.

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

3.  Fitness Factors for Bioorthogonal Chemical Probes.

Authors:  Yulin Tian; Qing Lin
Journal:  ACS Chem Biol       Date:  2019-12-05       Impact factor: 5.100

4.  Genetically encoded tetrazine amino acid directs rapid site-specific in vivo bioorthogonal ligation with trans-cyclooctenes.

Authors:  Jason L Seitchik; Jennifer C Peeler; Michael T Taylor; Melissa L Blackman; Timothy W Rhoads; Richard B Cooley; Christian Refakis; Joseph M Fox; Ryan A Mehl
Journal:  J Am Chem Soc       Date:  2012-02-01       Impact factor: 15.419

Review 5.  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

6.  Synthesis of macrocyclic tetrazoles for rapid photoinduced bioorthogonal 1,3-dipolar cycloaddition reactions.

Authors:  Zhipeng Yu; Reyna K V Lim; Qing Lin
Journal:  Chemistry       Date:  2010-12-03       Impact factor: 5.236

Review 7.  Photoclick chemistry: a fluorogenic light-triggered in vivo ligation reaction.

Authors:  Carlo P Ramil; Qing Lin
Journal:  Curr Opin Chem Biol       Date:  2014-07-11       Impact factor: 8.822

8.  Fine-Tuning Strain and Electronic Activation of Strain-Promoted 1,3-Dipolar Cycloadditions with Endocyclic Sulfamates in SNO-OCTs.

Authors:  Eileen G Burke; Brian Gold; Trish T Hoang; Ronald T Raines; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2017-05-31       Impact factor: 15.419

9.  Rapid, photoactivatable turn-on fluorescent probes based on an intramolecular photoclick reaction.

Authors:  Zhipeng Yu; Lok Yin Ho; Qing Lin
Journal:  J Am Chem Soc       Date:  2011-07-15       Impact factor: 15.419

10.  Photoinducible Oncometabolite Detection.

Authors:  Rhushikesh A Kulkarni; Chloe A Briney; Daniel R Crooks; Sarah E Bergholtz; Chandrasekhar Mushti; Stephen J Lockett; Andrew N Lane; Teresa W-M Fan; Rolf E Swenson; W Marston Linehan; Jordan L Meier
Journal:  Chembiochem       Date:  2018-12-13       Impact factor: 3.164
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