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Strain-Promoted Cycloadditions

The strain-promoted [3-1-2] cycloaddition reaction of substituted cyclooctyne with aryl azides furnishes 1,4,5-trisubstituted 1,2,3-triazoles, which have become good bioorthogonal probes. [Pg.87]

The azidophihc strained alkyne moiety of a cyclooctyne can be transiently masked via 1 1 complexation with a cationic copper salt, (MeCN)4CuBF4. [Pg.87]

Triazole-substituted titanocenes may be synthesized by a strain-driven 1,3-dipolar cycloadditions between azide-functionalized titanocenes and cyclooctyne. Titanocene derivative are interesting complexes since they are a promising class of cytotoxic compounds, efficient reagents and catalysts, and organometallic gelators. Azide-substituted cationic titanocenes reacted with cyclooctyne in CH2CI2 at room temperature to give the expected product with yields between 75% and 92% [84]. [Pg.87]

McKay CS, Blake JA, Cheng J, Danielson DC, Pezacki JP (2011) Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes for labeling human cancer cells. Chem Commun 47(36) 10040-10042. doi 10.1039/clccl3808a... [Pg.28]

Keywords Strain-promoted cycloaddition Cyclooctyne BCN DIBAC Azide... [Pg.60]

Plougastel L, Koniev O, Specklin S et al (2014) 4-Halogeno-sydnones for fast strain-promoted cycloaddition with bicyclo-[6.1.0]-nonyne. Chem Common 50 9376-9378... [Pg.78]

Singh I, Freeman C, Madder A, Vyle JS, Heaney F (2012) Fast RNA conjugations on solid phase by strain-promoted cycloadditions. Org Biomol Chem 10(33) 6633-6639. doi 10.1039/c2ob25628b... [Pg.153]

Figure 16 Cyclooctynes for strain-promoted cycloadditions with azides in living systems. Fluorination accelerates the cycloaddition because the electron-withdrawing fluoro substituents increase the reactivity of the ring-strained cyclooctyne. Figure 16 Cyclooctynes for strain-promoted cycloadditions with azides in living systems. Fluorination accelerates the cycloaddition because the electron-withdrawing fluoro substituents increase the reactivity of the ring-strained cyclooctyne.
A CPN-fused dibenzocyclooctyne 70 was prepared by Boons (Scheme 6.11). It undergoes fast strain-promoted cycloadditions with azides under catalyst-free conditions to yield a triazole 71, displaying more than 1000-fold brighter fluorescence than 70 [40]. [Pg.154]

Agard, N.J., Prcschcr, J.A., and Bertozzi, C.R. (2004) A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. /. Am. Chem. Soc. 126, 15046-15047. [Pg.1041]

Beatty KE, Fisk JD, Smart BP et al (2010) Live-cell imaging of cellular proteins by a strain-promoted azide-alkyne cycloaddition. Chembiochem 11 2092-2095... [Pg.36]

To date, four bioorthogonal reactions have been used to label glycans on cells and in lysates hydrazone/oxime formation with ketones, thiol alkylation with maleimides, Staudinger ligation of azides with triaryl phosphines, and copper-catalyzed or strain-promoted [3+2] cycloadditions of alkynes and azides (Figure 5) (25, 26, 32, 34, 35). While each reaction has been used extensively, most recent applications have employed azido- or alkynyl-sugars due to their superior metabolic incorporation and efficient ligations. [Pg.260]

Figure 5. Bioorthogonal reactions on sugars, A. Ketones react with hydrazides to give hydrazones. B. Thiols undergo Michael Reaction with maleimides. C, Azides undergo Staudinger ligation with phosphines or D. strain-promoted or copper catalyzed [3 2] cycloaddition with all nes. E. Alkynes undergo copper-catalyzed [3- 2] cycloaddition with azides. Figure 5. Bioorthogonal reactions on sugars, A. Ketones react with hydrazides to give hydrazones. B. Thiols undergo Michael Reaction with maleimides. C, Azides undergo Staudinger ligation with phosphines or D. strain-promoted or copper catalyzed [3 2] cycloaddition with all nes. E. Alkynes undergo copper-catalyzed [3- 2] cycloaddition with azides.
Fig. 10.3-20 Metal-free bioconjugation using a strain-promoted [3 + 2] dipolar cycloaddition reaction. This reaction is accelerated by the relief of ring strain in the transition state as the alkyne carbons become sp2 hybridized. Fig. 10.3-20 Metal-free bioconjugation using a strain-promoted [3 + 2] dipolar cycloaddition reaction. This reaction is accelerated by the relief of ring strain in the transition state as the alkyne carbons become sp2 hybridized.
POC-click is formed by thermo-cross-linking the mixture of pre-POC-N (azide-containing POC prepolymer) and pre-POC-Al (alkyne-containing POC prepolymer) the process applies synchronous binary cross-link mechanism, esterification, and thermal click reaction, and the residual azide groups on the surface of POC-click film or scaffold paved the way of surface bioconjugation through strain-promoted alkyne-azide cycloaddition (SPAAC), another copper-free click reaction. [Pg.263]

Recent advances and applications of strain-promoted alkyne-nitrone cycloaddition reactions in bio-orthogonal labeling (14COCB81) and of natural isoxazoline derivatives in the field of anticancer research (14EJM121) were reviewed. [Pg.327]

Strain-promoted alkyne-nitrone cycloaddition (SPANC) is another example of a 1,3-dipolar cycloaddition that has been applied for biomolecule labeling. The reactivity of nitrones with strained alkynes can be finely tuned by varying the substitution pattern [46-48]. Various cyclic nitrones were found to react with superior kinetics when compared to their acyclic counterparts and were successfully... [Pg.18]

Mckay CS, Moran J, Pezacki JP (2010) Nitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes. Chem Commun 46(6) 931-933. doi 10.1039/b921630h... [Pg.28]

McKay CS, Chigrinova M, Blake JA, Pezacki JP (2012) Kinetics studies of rapid strain-promoted [3 -H 2]-cycloadditions of nitrones with biaiyl-aza-cyclooctynone. Org Biomol Chem 10(15) 3066-3070. doi 10.1039/c2ob07165g... [Pg.28]

Ning XH, Temming RP, Dommerholt J, Guo J, Ania DB, Debets MF, Wolfert MA, Boons GJ, van Delft FL (2010) Protein modification by strain-promoted alkyne-nitrone cycloaddition. Angew Chem Int Ed 49(17) 3065-3068. doi 10.1002/anie.201000408... [Pg.28]

Temming RP, Eggermont L, van Eldijk MB, van Hest JCM, van Delft FL (2013) N-terminal dual protein functionalization by strain-promoted alkyne-nitrone cycloaddition. Org Biomol Chem 11(17) 2772-2779. doi 10.1039/c3ob00043e... [Pg.28]

Wallace S, Chin JW (2014) Strain-promoted sydnone bicyclo-[6.1.0]-nonyne cycloaddition. Chem Sci 5(5) 1742-1744. doi 10.1039/c3sc53332h... [Pg.29]

Friscourt F, Fahmi CJ, Boons G-J (2015) Fluorogenic strain-promoted alkyne-diazo cycloadditions. Chem A Eur J 21(40) 13996-14001. doi 10.1002/chem.201502242... [Pg.29]

See other pages where Strain-Promoted Cycloadditions is mentioned: [Pg.264]    [Pg.29]    [Pg.65]    [Pg.69]    [Pg.76]    [Pg.312]    [Pg.26]    [Pg.87]    [Pg.264]    [Pg.29]    [Pg.65]    [Pg.69]    [Pg.76]    [Pg.312]    [Pg.26]    [Pg.87]    [Pg.88]    [Pg.517]    [Pg.2183]    [Pg.275]    [Pg.253]    [Pg.267]    [Pg.227]    [Pg.228]    [Pg.185]    [Pg.459]    [Pg.354]    [Pg.18]    [Pg.32]   


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