Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones

Journal of the American Chemical Society

Volumn 132, Issue 11, 2010, Pages 3688-3690

  Jewett, John C ^a   Sletten, Ellen M ^a   Bertozzi, Carolyn R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PROCESS; CHEMICAL EQUATIONS; CLICK CHEMISTRY; FLUORESCENCE IMAGING; GLYCANS; IN-VIVO IMAGING; LIVE CELL; NANOMOLAR CONCENTRATION; SIGNAL-TO-BACKGROUND RATIO; WASHING STEPS;

ACETYLENE; BIOLOGY; GRAFTING (CHEMICAL); NITROGEN COMPOUNDS; REACTION KINETICS;

SYNTHESIS (CHEMICAL);

COPPER; CYCLOOCTANE DERIVATIVE;

ANIMAL CELL; ARTICLE; CHEMICAL REACTION KINETICS; CHEMISTRY; CLICK CHEMISTRY; CROSS LINKING; NONHUMAN; OXIDATION; SYNTHESIS;

ALKYNES; ANIMALS; AZIDES; CELL SURVIVAL; CHO CELLS; COPPER; CRICETINAE; CRICETULUS; KINETICS; MOLECULAR IMAGING; POLYSACCHARIDES;

EID: 77949778625     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja100014q     Document Type: Article

References (30)

1. Sletten, E. M.; Bertozzi, C. R. Aneew. Chem., Int. Ed. 2009, 48, 6974-6998.
2. Prescher, J. A.; Bertozzi C. R. Nat. Chem. Biol. 2005, 1, 13-21.
3. Kele, P.; Li, X.; Link, M.; Nagy, K.; Hemer, A.; Lonncz, K.; Bern, S.; Wolfbeis. O. S. Org. Biomol. Chem. 2009, 7, 3486-3490.
4. wolbers, F.; ter Braak, P.; Le Gac, S.; Luttge, R.; Andersson, H.; Vermes, I.; van den Berg, A. Electrophoresis 2006, 27, 5073.
5. For a recent review of all bioorthogonal Cu-free click cycloadditions, see: Jewett, J. C.; Bertozzi, C. R. Chem. Soc. Rev. 2010, in press DOI: 10.1039/ B901970G.
6. 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.
7. Johnson, J. A.; Baskin, J. M.; Bertozzi, C. R.; Koberstein, J. T.; Turro, N. J. Chem. Commun. 2008, 3064-3066.
8. Laughlin, S. T.; Baskin, J. M.; Amacher, S. L.; Bertozzi, C. R. Science 2008, 320, 664-667.
9. Ning, X.; Guo, J.; Wolfert, M. A.; Boons, G.-J. Angew. Chem. Int. Ed. 2008 47 2253-2255.
10. Ess, D. H.; Jones, G.O.; Houk, K. N. Org. Lett. 2008, 70, 1633-1636.
11. -1 (ref 6).
12. Debets, M. F.; van Berkel, S. S.; Schoffeien, S.; Rutjes, F. P. J. T.; van Hest, J. C. M.; van Delft, F. L. Chem. Commun. 2010, 46, 97-99.
13. (a) Wong, H. N. C.; Garratt, P. J.; Sondheimer, F. J. Am. Chem. Soc. 1974, 96, 5604-5605.
14. (b) Gugel, H; Meier, H. Chem. Ber. 1980. 113. 1431-1443.
15. Sletten, E. M.; Bertozzi, C. R. Org. Lett. 2008, 10, 3097-3099.
16. Chang, P. V.; Prescher, J. A.; Sletten, M.; Baskin, J. M.; Miller, I. A.; Agard, N. J.; Lo, A.; Bertozzi, C.R. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 1821-1826.
17. (a) Agard, N. J.; Prescher, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2004, 126, 15046-21504
18. (b) Codelli, J. A.; Baskin, J. M.; Agard, N. J.; Bertozzi, G R. J. Am. Chem. Soc. 2008, 130 11486-11493.
19. For a recent paper that addresses this problem, see: Poloukhtine, A. A.; Mbua, N. E.; Wolfert, M. A.; Boons, G.-J.; Popik, V. V. J. Am. Chem. Soc. 2009, 131, 15769-15776.
20. Atanes, N.; Escudero, S.; Pérez, D.; Guitián, E.; Castedo, L. Tetrahedron Lett. 1998, 39, 3039-3040.
21. Sampson, P.; Wiemer, D. F. J. Chem. Soc. Chem. Commun. 1985, 1746-1747.
22. Letcher, R. M.; Kwok, N.-C.; Lo, W.-H.; Ng, K. W.J. Perkin Trans.1 1998, 1715-1719.
23. (a) Abraham, T. Monat. Fur̈ Chemie 1989, 120, 117-126
24. (b) Grandini, C.; Camurati, I.; Guidotti, S.; Mascellam, N.; Resconi, L.; Nliant'ev, I. E.; Kashulin, I. A.; Ivchenko, P. V.; Mercandelli, P.; Sironi, A. Oreanometallics 2004, 23, 344-360.
25. Okamoto, T. A.; Kobayashi, S. M.; Yamamoto, H. N. German Pat. DE1952019 1970.
26. Nifant'ev, I. E.; Kashulin, I. A.; Bagrov, V. V.; Abilev, S. K.; Lyubimova, I.K. Russ. Chem. Bull. 2001, 50, 1439-1445.
27. (a) For an early review on this type of reaction, see: Huisgen, R. Aneew. Chem., Int. Ed. 1963, 2, 565-598.
28. (b) For a recent application of this chemistry, see: Gutsmiedl, K. ; Wirges, C. T.; Ehmke, V.; Carell, T. Org. Lett. 2009, 11, 2405-2408.
29. 2O (1:2) was 24 h at rt.
30. Laughlin, S. T.; Bertozzi, C. R. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 12-17.