Strain-promoted sydnone bicyclo-[6.1.0]-nonyne cycloaddition

Wallace, Stephen; Chin, Jason W.

doi:10.1039/c3sc53332h

Cited by 104 publications

(66 citation statements)

References 45 publications

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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%

“…Additionally, syndones have been used as 1,3-dipoles in Cu I catalyzed cycloadditions with terminal alkynes (Kolodych et al, 2013), and more recently in strain-promoted cycloadditions with bicyclononyne (rate constant = 0.054 M −1 s −1 , comparable with that of azides). This method was applied to the efficient fluorescent tagging of cyclooctyne-modified proteins (Wallace and Chin, 2014). Recently, the rate of this cycloaddition process has been improved 30-fold by using 4-chlorosyndones ( k 2 = 1.6 M −1 s −1 ) (Taran 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

655

555

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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

655

555

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“…Similarly, both our laboratory [27] and Sanders et al [47] reported the reaction of cyclooctynes with nitrile oxides (SPANOC) leading to isoxazoles, which is a factor *10 faster than SPAAC and SPANC. Finally, strain-promoted cycloaddition with diazo-compounds is also known [47] as well as reaction of BCN with sydnone [42,61]. Interestingly, in the field of (4 ?…”

Section: Concluding Remarks and Future Prospectsmentioning

confidence: 99%

Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides

Dommerholt

Rutjes

Delft

2016

Cycloadditions in Bioorthogonal Chemistry

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A nearly forgotten reaction discovered more than 60 years ago-the cycloaddition of a cyclic alkyne and an organic azide, leading to an aromatic triazole-enjoys a remarkable popularity. Originally discovered out of pure chemical curiosity, and dusted off early this century as an efficient and clean bioconjugation tool, the usefulness of cyclooctyne-azide cycloaddition is now adopted in a wide range of fields of chemical science and beyond. Its ease of operation, broad solvent compatibility, 100 % atom efficiency, and the high stability of the resulting triazole product, just to name a few aspects, have catapulted this so-called strain-promoted azide-alkyne cycloaddition (SPAAC) right into the top-shelf of the toolbox of chemical biologists, material scientists, biotechnologists, medicinal chemists, and more. In this chapter, a brief historic overview of cycloalkynes is provided first, along with the main synthetic strategies to prepare cycloalkynes and their chemical reactivities. Core aspects of the strain-promoted reaction of cycloalkynes with azides are covered, as well as tools to achieve further reaction acceleration by means of modulation of cycloalkyne structure, nature of azide, and choice of solvent.

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“…[1] Thec opper-catalyzed (CuAAC) and strain-promoted (SPAAC) azide-alkyne cycloaddition reactions are possibly the most commonly used click reactions for in vitro as well as in vivo ligation applications. [7] Thec opper-free version of this reaction was reported by the group of J. W. Chin [8] and by J. M. Murphy and co-workers. [7] Thec opper-free version of this reaction was reported by the group of J. W. Chin [8] and by J. M. Murphy and co-workers.…”

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confidence: 99%

Ultrafast Click Chemistry with Fluorosydnones

et al. 2016

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We report the synthesis and reactivity of 4-fluorosydnones, a unique class of mesoionic dipoles displaying exquisite reactivity towards both copper-catalyzed and strain-promoted cycloaddition reactions with alkynes. Synthetic access to these new mesoionic compounds was granted by electrophilic fluorination of σ-sydnone Pd(II) precursors in the presence of Selectfluor. Their reactions with terminal and cyclic alkynes were found to proceed very rapidly and selectively, affording 5-fluoro-1,4-pyrazoles with bimolecular rate constants up to 10(4) m(-1) s(-1) , surpassing those documented in the literature with cycloalkynes. Kinetic studies were carried out to unravel the mechanism of the reaction, and the value of 4-fluorosydnones was further highlighted by successful radiolabeling with [(18) F]Selectfluor.

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Strain-promoted sydnone bicyclo-[6.1.0]-nonyne cycloaddition

Abstract: We report the strain-promoted sydnone bicyclo-[6.1.0]-nonyne cycloaddition and demonstrate that this bioorthogonal reaction enables site-specific protein labelling.

Cited by 104 publications

References 45 publications

Click Chemistry in Complex Mixtures: Bioorthogonal Bioconjugation

Click Chemistry in Complex Mixtures: Bioorthogonal Bioconjugation

Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides

Ultrafast Click Chemistry with Fluorosydnones

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