Copper-Free “Click” Modification of DNA via Nitrile Oxide−Norbornene 1,3-Dipolar Cycloaddition

Gutsmiedl, Katrin; Wirges, Christian T.; Ehmke, Veronika; Carell, Thomas

doi:10.1021/ol9005322

Cited by 141 publications

(114 citation statements)

References 40 publications

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“…The cycloadditions of strained alkynes or alkenes with nitrile oxide have also been investigated recently (Gutsmiedl et al, 2009). The reaction also occurred with an unstrained alkyne and in situ formation of the nitrile oxide by hypervalent iodine, but was sluggish (Jawalekar et al, 2011).…”

Section: Metal-freementioning

confidence: 99%

Protein Engineering with Non-Natural Amino Acids

Wang¹,

Nairn²,

Marelli³

et al. 2012

Protein Engineering

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Section: Metal-freementioning

confidence: 99%

Protein Engineering with Non-Natural Amino Acids

Wang¹,

Nairn²,

Marelli³

et al. 2012

Protein Engineering

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“…8 Extensive effort has been devoted to overcome such drawbacks, resulting in the development of metal-free azide-alkyne click chemistry as well as azide-free click chemistry. [9][10][11][12][13][14][15] Nevertheless, the drawbacks arising from triazole ring formation have not yet been solved.…”

Section: Introductionmentioning

confidence: 99%

High-performance triazole-containing brush polymers via azide–alkyne click chemistry: a new functional polymer platform for electrical memory devices

Song

Lee

et al. 2015

NPG Asia Mater

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Two series of well-defined brush polymers bearing a triazole moiety on each bristle were prepared from the click chemistry reactions of a poly(glycidyl azide) (PG) and a poly(4-azidomethylstyrene) (PS) with alkyne derivatives. The thin-film morphologies and properties, especially electrical memory performances, of these triazole-containing brush polymers were investigated in detail. The brush polymers with a triazole ring substituted with an alkyl or alkylenylphenyl group in the bristle exhibited only dielectric characteristics. By contrast, the other brush polymers bearing a triazole ring substituted with phenyl or its derivatives with a longer π-conjugation length in the bristle demonstrated excellent unipolar permanent memory behaviors with low power consumption, high ON/OFF current ratios and high stability and reliability under ambient air conditions. Furthermore, their memory type could be tuned to p-or n-type by the incorporation of an electron-donating or -accepting group into the phenyl unit linked to the triazole moiety. Overall, this study presents the first demonstration of the azide-alkyne click chemistry synthesis of triazole moieties with substituent(s) that exhibit a resonance effect; this approach is a very powerful synthetic route to develop electrical memory polymers suitable for the low-cost mass production of high-performance, polarity-free programmable memory devices.

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“…We and others have reported the application of nitrile oxide derivatives to the modification of nucleosides, oligonucleotides and polymers bearing alkene/alkyne functions. [13][14][15][16][17][18][19] Other metal-free strategies include Diels-Alder cycloadditions, 20 photoinduceable cycloadditions of tetrazines or nitrile imines to alkenes 21,22 and strain-promoted azide-alkyne cycloaddition (SPAAC) reactions.…”

Section: Introductionmentioning

confidence: 99%

Fast RNA conjugations on solid phase by strain-promoted cycloadditions

et al. 2012

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Strain promoted cycloaddition is presented as a tool for RNA conjugation on the solid phase; RNA-cyclooctyne conjugates are prepared by cycloaddition to both azide (strain-promoted azide-alkyne cycloaddition, SPAAC) and nitrile oxide dipoles (strain-promoted nitrile oxide-alkyne cycloaddition, SPNOAC). The conjugation is compatible with 2′-OMe blocks and with 2′-O-TBDMS protection on the ribose moieties of the sugar. Nitrile oxide dipoles are found to be more reactive click partners than azides. The conjugation proceeds within 10 min in aqueous solvents, at room temperature without any metal catalyst and tolerates dipoles of varying steric bulk and electronic demands, including pyrenyl, coumarin and dabcyl derivatives.

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Copper-Free “Click” Modification of DNA via Nitrile Oxide−Norbornene 1,3-Dipolar Cycloaddition

Cited by 141 publications

References 40 publications

Protein Engineering with Non-Natural Amino Acids

Protein Engineering with Non-Natural Amino Acids

High-performance triazole-containing brush polymers via azide–alkyne click chemistry: a new functional polymer platform for electrical memory devices

Fast RNA conjugations on solid phase by strain-promoted cycloadditions

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