Synthesis of a fluorogenic cyclooctyne activated by Cu-free click chemistry

Organic Letters

Volumn 13, Issue 22, 2011, Pages 5937-5939

  Jewett, John C ^a   Bertozzi, Carolyn R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; CYCLOOCTANE; CYCLOOCTANE DERIVATIVE; FLUORESCENT DYE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CLICK CHEMISTRY; SYNTHESIS;

CLICK CHEMISTRY; COPPER; CYCLOOCTANES; FLUORESCENT DYES; MOLECULAR STRUCTURE;

EID: 80955129969     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2025026     Document Type: Article

References (24)

1. Sadhu, K. K.; Mizukami, S.; Hori, Y.; Kikuchi, K. ChemBioChem 2011, 12, 1299-1308
2. Hilderbrand, S. A.; Kelly, K. A.; Niedre, M.; Weissleder, R. Bioconjugate Chem. 2008, 19, 1635-1639
3. Sletten, E. M.; Bertozzi, C. R. Acc. Chem. Res. 2011, 44, 666-676
4. Saxon, E.; Bertozzi, C. R. Science 2000, 287, 2007-2010
5. Agard, N. J.; Prescher, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2004, 126, 15046-15047
6. Lemieux, G. A.; de Graffenried, C. L.; Bertozzi, C. R. J. Am. Chem. Soc. 2003, 125, 4708-4709
7. Hangauer, M. J.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2008, 47, 2394-2397
8. Baskin, J. M.; Prescher, J. A.; Laughlin, S. T.; Agard, N. J.; Chang, P. V.; Miller, I. A.; Lo, A.; Codelli, J. A.; Bertozzi, C. R. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 16793-16797
9. Ning, X.; Guo, J.; Wolfert, M. A.; Boons, G.-J. Angew. Chem., Int. Ed. 2008, 47, 2253-2255
10. Debets, M. F.; van Berkel, S. S.; Schoffelen, S.; Rutjes, F. P. J. T.; van Hest, J. C. M.; van Delft, F. L. Chem. Commun. 2010, 46, 97-99
11. Jewett, J. C.; Sletten, E. M.; Bertozzi, C. R. J. Am. Chem. Soc. 2010, 132, 3688-3690
12. Dommerholt, J.; Schmidt, S.; Temming, S.; Hendriks, L. J. A.; Rutjes, F. P. J. T.; van Hest, J. C. M.; Lefeber, D. J.; Friedl, P.; van Delft, F. L. Angew. Chem., Int. Ed. 2010, 49, 9422-9425
13. Sletten, E. M.; Bertozzi, C. R. Org. Lett. 2008, 10, 3097-3099
14. Stöckmann, H.; Neves, A. A.; Stairs, S.; Ireland-Zecchini, H.; Brindle, K. M.; Leeper, F. J. Chem. Sci. 2011, 2, 932-936
15. Le Droumaguet, C.; Wang, C.; Wang, Q. Chem. Soc. Rev. 2010, 39, 1233-1239
16. Zhou, Z.; Fahrni, C. J. J. Am. Chem. Soc. 2004, 126, 8862-8863
17. Mbua, N. E.; Guo, J.; Wolfert, M. A.; Steet, R.; Boons, G.-J. ChemBioChem 2011, 12, 1912-1921
18. Kleinpeter, E.; Wilde, H.; Hauptmann, S. Magn. Reson. Chem. 1986, 24, 53-54
19. Schiedel, M.-S.; Briehn, C. A.; Bäuerle, P. J. Organomet. Chem. 2002, 653, 200-208
20. The 4-phenylcoumarin moiety has shown success in other fluorogenic applications, albeit with a different turn-on mechanism. See: Do, J. H.; Kim, H. N.; Yoon, J.; Kim, J. S.; Kim, H.-J. Org. Lett. 2010, 12, 932-934
21. Brown, D. W.; Graupner, P. R.; Sainsbury, M.; Shertzer, H. G. Tetrahedron 1991, 47, 4383-4408
22. Sundberg, R. J.; Parton, R. L. J. Org. Chem. 1976, 41, 163-165
23. Plazuk, D.; Zakrzewski, J. J. Org. Chem. 2002, 67, 8672-8674
24. Peña, D.; Cobas, A.; Pérez, D.; Guitián, E. Synthesis 2002, 10, 1454-1458