Literature DB >> 26538499

Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking.

Dewey A Sutton1, Seok-Ho Yu, Richard Steet, Vladimir V Popik.   

Abstract

The first fully conjugated bis-cyclopropenone (photo-DIBOD), a derivative of dibenzo[a,e][8]annulene, has been synthesized. 350-420 nm irradiation of this robust compound results in the efficient formation of dibenzo [a,e] cyclooctadiyne, an unstable, but useful SPAAC cross-linking reagent. Since photo-DIBO doesn't react with organic azides, this method allows for the spatiotemporal control of the ligation of two azide-tagged substrates.

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Year:  2015        PMID： 26538499      PMCID： PMC4689622          DOI： 10.1039/c5cc08106h

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


  52 in total

Review 1.  Efficient Photochemical Approaches for Spatially Resolved Surface Functionalization.

Authors:  Guillaume Delaittre; Anja S Goldmann; Jan O Mueller; Christopher Barner-Kowollik
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-01       Impact factor: 15.336

2.  Propargyl amides as irreversible inhibitors of cysteine proteases--a lesson on the biological reactivity of alkynes.

Authors:  Christoph Arkona; Jörg Rademann
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-21       Impact factor: 15.336

Review 3.  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

4.  Two-photon photochemical generation of reactive enediyne.

Authors:  Andrei Poloukhtine; Vladimir V Popik
Journal:  J Org Chem       Date:  2006-09-15       Impact factor: 4.354

5.  A fluorogenic probe for the catalyst-free detection of azide-tagged molecules.

Authors:  Frédéric Friscourt; Christoph J Fahrni; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2012-11-02       Impact factor: 15.419

6.  Robust, efficient, and orthogonal synthesis of dendrimers via thiol-ene "click" chemistry.

Authors:  Kato L Killops; Luis M Campos; Craig J Hawker
Journal:  J Am Chem Soc       Date:  2008-03-20       Impact factor: 15.419

7.  Photoinduced thiol-ene coupling as a click ligation tool for thiodisaccharide synthesis.

Authors:  Michele Fiore; Alberto Marra; Alessandro Dondoni
Journal:  J Org Chem       Date:  2009-06-05       Impact factor: 4.354

Review 8.  Copper toxicity, oxidative stress, and antioxidant nutrients.

Authors:  Lisa M Gaetke; Ching Kuang Chow
Journal:  Toxicology       Date:  2003-07-15       Impact factor: 4.221

9.  Fluorogenic, two-photon-triggered photoclick chemistry in live mammalian cells.

Authors:  Zhipeng Yu; Tymish Y Ohulchanskyy; Peng An; Paras N Prasad; Qing Lin
Journal:  J Am Chem Soc       Date:  2013-10-31       Impact factor: 15.419

10.  Sequential "click" - "photo-click" cross-linker for catalyst-free ligation of azide-tagged substrates.

Authors:  Selvanathan Arumugam; Vladimir V Popik
Journal:  J Org Chem       Date:  2014-02-28       Impact factor: 4.354
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  3 in total

1.  Sequential Photochemistry of Dibenzo[a,e]dicyclopropa[c,g][8]annulene-1,6-dione: Selective Formation of Didehydrodibenzo[a,e][8]annulenes with Ultrafast SPAAC Reactivity.

Authors:  Dewey A Sutton; Vladimir V Popik
Journal:  J Org Chem       Date:  2016-09-29       Impact factor: 4.354

Review 2.  Light-Triggered Click Chemistry.

Authors:  Gangam Srikanth Kumar; Qing Lin
Journal:  Chem Rev       Date:  2020-10-26       Impact factor: 72.087

Review 3.  Photo-induced and Rapid Labeling of Tetrazine-Bearing Proteins via Cyclopropenone-Caged Bicyclononynes.

Authors:  Susanne V Mayer; Anton Murnauer; Marie-Kristin von Wrisberg; Marie-Lena Jokisch; Kathrin Lang
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-24       Impact factor: 15.336
  3 in total

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