Protein Modification by Strain‐Promoted Alkyne–Nitrone Cycloaddition

Ning, Xinghai; Temming, Rinske P.; Dommerholt, Jan; Guo, Jun; Ania, Daniel B.; Debets, Marjoke F.; Wolfert, Margreet A.; Boons, Geert‐Jan; Delft, Floris L. van

doi:10.1002/anie.201000408

Cited by 201 publications

(133 citation statements)

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“…Alternative 1,3-dipoles such as nitrones (McKay et al, 2011; McKay et al, 2010; Ning et al, 2010), nitrile oxides (Sanders et al, 2011; Singh and Heaney, 2011), diazoalkanes (McGrath and Raines, 2012), and syndones (Wallace and Chin, 2014) have also been explored as means for improving the kinetics and biocompatibility of reactions with multiple-bond partners (primarily strained alkynes, Figure 5E). Strain-promoted alkyne-nitrone cycloaddition (SPANC) reactions demonstrate rate constants up to 60 M −1 s −1 (McKay et al, 2012; McKay et al, 2010; Ning et al, 2010), and have been used for N -terminal peptide modification (Ning et al, 2010), direct protein labeling, and pre-targeted labeling of ligand-receptor interactions on cell surfaces (McKay et al, 2011).…”

Section: B Bioorthogonal Conjugation Strategies and Applicationsmentioning

confidence: 99%

“…Strain-promoted alkyne-nitrone cycloaddition (SPANC) reactions demonstrate rate constants up to 60 M −1 s −1 (McKay et al, 2012; McKay et al, 2010; Ning et al, 2010), and have been used for N -terminal peptide modification (Ning et al, 2010), direct protein labeling, and pre-targeted labeling of ligand-receptor interactions on cell surfaces (McKay et al, 2011). Cyclic nitrones display greater stability toward hydrolysis and faster kinetics than their acyclic counterparts, and nitrone reactivity is tunable to allow for simultaneous SPANC reactions for multiplex labeling (MacKenzie and Pezacki, 2014; MacKenzie et al, 2014).…”

Section: B Bioorthogonal Conjugation Strategies and Applicationsmentioning

confidence: 99%

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Click Chemistry in Complex Mixtures: Bioorthogonal Bioconjugation

McKay

Finn

2014

Chemistry & Biology

641

550

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The selective chemical modification of biological molecules drives a good portion of modern drug development and fundamental biological research. While a few early examples of reactions that engage amine and thiol groups on proteins helped establish the value of such processes, the development of reactions that avoid most biological molecules so as to achieve selectivity in desired bond-forming events has revolutionized the field. We provide an update on recent developments in bioorthogonal chemistry that highlights key advances in reaction rates, biocompatibility, and applications. While not exhaustive, we hope this summary allows the reader to appreciate the rich continuing development of good chemistry that operates in the biological setting.

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Section: B Bioorthogonal Conjugation Strategies and Applicationsmentioning

confidence: 99%

Section: B Bioorthogonal Conjugation Strategies and Applicationsmentioning

confidence: 99%

Click Chemistry in Complex Mixtures: Bioorthogonal Bioconjugation

McKay

Finn

2014

Chemistry & Biology

641

550

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“…For example, the biarylazacyclooctyne reported by Boons and Popik was associated with a rate-constant of 0.31 M -1 s -1 . 37, 51, 52 …”

Section: Resultsmentioning

confidence: 99%

In Vivo Virus-Based Macrofluorogenic Probes Target Azide-Labeled Surface Glycans in MCF-7 Breast Cancer Cells

et al. 2012

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Chemical addressability of viral particles has played a pivotal role in adapting these biogenic macromolecules for various applications ranging from medicine to inorganic catalysis. The consistent multimeric assemblies dictated by its genetic code, facile large scale production, lack of observable toxicity in humans, Cowpea mosaic virus possesses multiple features that are advantageous for the next generation of virus-based nanotechnology. Herein, the chemistry of the viral particles is extended with the use of Cu-free strain-promoted azide-alkyne cycloaddition reaction, or SPAAC reaction. The elimination of Cu, its co-catalyst and reducing agent simplifies the reaction scheme to a more straightforward approach, which can be directly applied to living systems. As a proof of concept, the viral particles modified with the aza-dibenzylcyclooctynes functional groups are utilized to trigger and amplify a weak fluorescent signal (azidocoumarin) in live cell cultures to visualize the non-natural sugars. Future adaptations of this platform may be developed to enhance biosensing applications.

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“…14 We recently developed a straightforward route to a novel cyclooctyne analogue, namely bicyclo[6.1.0]nonyne (BCN), for metal-free cycloaddition reactions. 15 In this context, the cycloaddition of BCN with nitrile oxide could constitute another versatile metal-free ligation strategy.…”

Section: Abmentioning

confidence: 99%