Click imaging of biochemical processes in living systems

ACS Chemical Biology

Volumn 2, Issue 12, 2007, Pages 775-778

  Fokin, Valery V ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; AZIDE; COPPER; DYE; FUNCTIONAL GROUP; GLYCAN DERIVATIVE; GLYCOCONJUGATE; NUCLEIC ACID; POLYMER; PROTEIN; WATER;

ARTICLE; BIOSYNTHESIS; CARBOHYDRATE TRANSPORT; CELL LABELING; CELL LEVEL; CELL MEMBRANE; CELL SURFACE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLOADDITION; CYTOTOXICITY; ESCHERICHIA COLI; FLOW CYTOMETRY; FLUORESCENCE MICROSCOPY; HUMAN; HYDROGEN BOND; IMAGE ANALYSIS; INCUBATION TIME; INTERNALIZATION; MAMMAL CELL; METABOLIC ENGINEERING; METABOLISM; METABOLITE; MOLECULAR BIOLOGY; NONHUMAN; PRIORITY JOURNAL; STAUDINGER REACTION; TISSUE DISTRIBUTION; VIRUS PARTICLE;

BIOCHEMISTRY; CELL SURVIVAL;

EID: 38649096952     PISSN: 15548929     EISSN: None     Source Type: Journal    
DOI: 10.1021/cb700254v     Document Type: Article

References (28)

1. Baskin, J. M., Prescher, J. A., Laughlin, S. T., Agard, N. J., Chang, P. V., Miller, I. A., Lo, A., Codelli, J. A., and Bertozzi, C. R. (2007) Copper-free click chemistry for dynamic in vivo imaging, Proc. Natl. Acad. Sci. U.S.A. 104, 16793-16797.
2. Saxon, E., and Bertozzi, C. R. (2000) Cell surface engineering by a modified Staudinger reaction, Science 287, 2007-2010.
3. Hang, H. C., Yu, C., Kato, D. L., and Bertozzi, C. R. (2003) A metabolic labeling approach toward proteomic analysis of mucin-type O-linked glycosylation, Proc. Natl. Acad. Sci. U.S.A. 100, 14846-14851.
4. Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40, 2004-2021.
5. Michael, A. (1893) J. Prakt. Chem. 48, 94.
6. Huisgen, R. (1989) Kinetics and reaction mechanisms: selected examples from the experience of forty years, Pure Appl. Chem. 61, 613-628.
7. Huisgen, R. (1984) 1,3-Dipolar cycloaddition-introduction, survey, mechanism, in 1,3-Dipolar Cycloaddition Chemisty (Padwa, A., Ed.). pp 1-176, Wiley, New York.
8. Himo, F., Lovell, T., Hilgraf, R., Rostovtsev, V. V., Noodleman, L., Sharpless, K. B., and Fokin, V. V. (2005) Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates, J. Am. Chem. Soc. 127, 210-216.
9. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes, Angew. Chem., Int. Ed. 41, 2596-2599.
10. Tarnøe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to asides, J. Org. Chem. 67, 3057-3062.
11. Wu, P., and Fokin, V. V. (2007) Catalytic azide-alkyne cycloaddition: reactivity and applications, Aldrichimica Acta 40, 7-17.
12. Tome, A. C. (2004) Product class 13: 1,2,3-triazoles, in Science of Synthesis (Storr, R. C., and Gilchrist, T. L., Eds.), pp 415-601, Thieme, Stuttgart and New York.
13. Krivopalov, V. P., and Shkurko, O. P. (2005) 1,2,3-Triazole and its derivatives. Development of methods for the formation of the triazole ring. Russ. Chem. Rev. 74, 339-379.
14. Wang, Q., Chan, T. R., Hilgraf, R., Fokin, V. V., Sharpless, K. B., and Finn, M. G. (2003) Bioconjugation by copper(I)-catalyzed azide-alkyne [3+2] cycloaddition, J. Am. Chem. Soc. 125, 3192-3193.
15. Link, A. J., and Tirrell, D. A. (2003) Cell surface labeling of Escherichia coli via copper(I)-catalyzed [3+2] cycloaddition, J. Am. Chem. Soc. 125, 11164-11165.
16. Link, A. J., Vink, M. K. S., and Tirrell, D. A. (2004) Presentation and detection of aside functionality in bacterial cell surface proteins, J. Am. Chem. Soc. 126, 10598-10602.
17. Speers, A. E., Adam, G. C., and Cravatt, B. F. (2003) Activity-based protein profiling in vivo using a copper(I)-catalyzed azide-alkyne [3+2] cycloaddition, J. Am. Chem. Soc. 125, 4686-4687.
18. Bock, V. D., Hiemstra, H., and van Maarseveen, J. H. (2006) Cu(I)-catalyzed alkyne-azide click cycloadditions from a mechanistic and synthetic perspective, Eur. J. Org. Chem. 51-68.
19. Goodall, G. W., and Hayes, W. (2006) Advances in cycloaddition polymerizations, Chem. Soc. Rev. 35, 280-312.
20. Graham, D., and Enright, A. (2006) Cycloadditions as a method for oligonucleotide conjugation, Curr. Org. Synth. 3, 9-17.
21. Kolb, H. C., and Sharpless, K. B. (2003) The growing impact of click chemistry on drug discovery. Drug Discovery Today 8, 1128-1137.
22. Wang, Q., Chittaboina, S., and Bamhill, H. N. (2005) Advances in 1,3-dipolar cycloaddition reaction of azides and alkynes-a prototype of "click" chemistry, Lett. Org. Chem. 2, 293-301.
23. Beatty, K. E., Xie, F., Wang, Q., and Tirrell, D. A. (2005) Selective dye-labeling of newly synthesized proteins in bacterial cells, J. Am. Chem. Soc. 127, 14150-14151.
24. Speers, A. E., and Cravatt, B. F. (2004) Chemical strategies for activity-based proteomics, ChemBio-Chem 5, 41-47.
25. Agard, N. J., Prescher, J. A., and Bertozzi, C. R. (2004) A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J. Am. Chem. Soc. 126, 15046-15047.
26. Wittig, G., and Krebs, A. (1961) Chem. Ber. 94, 3260-3275.
27. Agard, N. J., Baskin, J. M., Prescher, J. A., Lo, A., and Bertozzi, C. R. (2006) A comparative study of bioorthogonal reactions with azides, ACS Chem. Biol. 1, 644-648.
28. Saxon, E., Luchansky, S. J., Hang, H. C., Yu, C., Lee, S. C., and Bertozzi, C. R. (2002) Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation, J. Am. Chem. Soc. 124, 14893-14902.