Literature DB >> 22987146

Photochemical generation of oxa-dibenzocyclooctyne (ODIBO) for metal-free click ligations.

Christopher D McNitt1, Vladimir V Popik.   

Abstract

Oxa-dibenzocyclooctynes (ODIBO, 2a-c) are prepared by photochemical decarbonylation of corresponding cyclopropenones (photo-ODIBO, 1a-c). While photo-ODIBO does not react with azides, ODIBO is one of the most reactive cyclooctynes exhibiting rates of cycloaddition over 45 M(-1) s(-1) in aqueous solutions. ODIBO is stable under ambient conditions and has low reactivity towards thiols. Photo-ODIBO survives heating up to 160 °C and does not react with thiols.

Entities:  

Year:  2012        PMID： 22987146      PMCID： PMC5992911          DOI： 10.1039/c2ob26581h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  25 in total

1.  A non-fluorinated monobenzocyclooctyne for rapid copper-free click reactions.

Authors:  Balázs R Varga; Mihály Kállay; Krisztina Hegyi; Szabolcs Béni; Péter Kele
Journal:  Chemistry       Date:  2011-12-20       Impact factor: 5.236

2.  High density orthogonal surface immobilization via photoactivated copper-free click chemistry.

Authors:  Sara V Orski; Andrei A Poloukhtine; Selvanathan Arumugam; Leidong Mao; Vladimir V Popik; Jason Locklin
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

Review 3.  Cu-free click cycloaddition reactions in chemical biology.

Authors:  John C Jewett; Carolyn R Bertozzi
Journal:  Chem Soc Rev       Date:  2010-04       Impact factor: 54.564

4.  Copper-free click chemistry in living animals.

Authors:  Pamela V Chang; Jennifer A Prescher; Ellen M Sletten; Jeremy M Baskin; Isaac A Miller; Nicholas J Agard; Anderson Lo; Carolyn R Bertozzi
Journal:  Proc Natl Acad Sci U S A       Date:  2010-01-14       Impact factor: 11.205

5.  Transition states of strain-promoted metal-free click chemistry: 1,3-dipolar cycloadditions of phenyl azide and cyclooctynes.

Authors:  Daniel H Ess; Gavin O Jones; K N Houk
Journal:  Org Lett       Date:  2008-03-26       Impact factor: 6.005

Review 6.  Copper toxicity, oxidative stress, and antioxidant nutrients.

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

7.  Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition.

Authors:  Qian Wang; Timothy R Chan; Robert Hilgraf; Valery V Fokin; K Barry Sharpless; M G Finn
Journal:  J Am Chem Soc       Date:  2003-03-19       Impact factor: 15.419

8.  Live-cell imaging of cellular proteins by a strain-promoted azide-alkyne cycloaddition.

Authors:  Kimberly E Beatty; John D Fisk; Brian P Smart; Ying Ying Lu; Janek Szychowski; Matthew J Hangauer; Jeremy M Baskin; Carolyn R Bertozzi; David A Tirrell
Journal:  Chembiochem       Date:  2010-10-18       Impact factor: 3.164

9.  Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells.

Authors:  Jan Dommerholt; Samuel Schmidt; Rinske Temming; Linda J A Hendriks; Floris P J T Rutjes; Jan C M van Hest; Dirk J Lefeber; Peter Friedl; Floris L van Delft
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

10.  Thiacycloalkynes for copper-free click chemistry.

Authors:  Gabriela de Almeida; Ellen M Sletten; Hitomi Nakamura; Krishnan K Palaniappan; Carolyn R Bertozzi
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-26       Impact factor: 15.336
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  12 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

2.  [18F]ODIBO: a prosthetic group for bioorthogonal radiolabeling of macromolecules via strain-promoted alkyne-azide cycloaddition.

Authors:  Mehdi Boudjemeline; Christopher D McNitt; Thomas A Singleton; Vladimir V Popik; Alexey P Kostikov
Journal:  Org Biomol Chem       Date:  2018-01-17       Impact factor: 3.876

3.  Artificial Membrane Fusion Triggered by Strain-Promoted Alkyne-Azide Cycloaddition.

Authors:  Stuart A Whitehead; Christopher D McNitt; Samuel I Mattern-Schain; Adam J Carr; Shahrina Alam; Vladimir V Popik; Michael D Best
Journal:  Bioconjug Chem       Date:  2017-03-14       Impact factor: 4.774

4.  Development of Dual Receptor Enhanced Pre-Targeting Strategy-A Novel Promising Technology for Immuno-Positron Emission Tomography Imaging.

Authors:  Lingyi Sun; Yongkang Gai; Zhonghan Li; Xiaohui Zhang; Jianchun Li; Yongyong Ma; Huiqiang Li; Ramon J Barajas; Dexing Zeng
Journal:  Adv Ther (Weinh)       Date:  2021-08-21

5.  Facile Quenching and Spatial Patterning of Cylooctynes via Strain-Promoted Alkyne-Azide Cycloaddition of Inorganic Azides.

Authors:  Matthew Bjerknes; Hazel Cheng; Christopher D McNitt; Vladimir V Popik
Journal:  Bioconjug Chem       Date:  2017-05-09       Impact factor: 4.774

6.  Photoactivatable fluorescein derivatives caged with a (3-hydroxy-2-naphthalenyl)methyl group.

Authors:  Emmanuel E Nekongo; Vladimir V Popik
Journal:  J Org Chem       Date:  2014-08-01       Impact factor: 4.354

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

Authors:  Dewey A Sutton; Seok-Ho Yu; Richard Steet; Vladimir V Popik
Journal:  Chem Commun (Camb)       Date:  2015-11-05       Impact factor: 6.222

Review 8.  Light-Triggered Click Chemistry.

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

9.  Ring Expansion of Alkylidenecarbenes Derived from Lactams, Lactones, and Thiolactones into Strained Heterocyclic Alkynes: A Theoretical Study.

Authors:  Nguyen Nhat Thu Le; Josefine Just; Jonathan M Pankauski; Paul R Rablen; Dasan M Thamattoor
Journal:  Molecules       Date:  2019-02-07       Impact factor: 4.411

10.  Photo-Click-Facilitated Screening Platform for the Development of Hetero-Bivalent Agents with High Potency.

Authors:  Lingyi Sun; Yongkang Gai; Christopher D McNitt; Jun Sun; Xiaohui Zhang; Wei Xing; Zhonghan Li; Vladimir V Popik; Dexing Zeng
Journal:  J Org Chem       Date:  2020-04-07       Impact factor: 4.354
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