Synthesis 2012; 44(13): 2005-2012
DOI: 10.1055/s-0031-1291145
paper
© Georg Thieme Verlag Stuttgart · New York

Fluorescence Labeling of Amino Acids and Peptides with 7-Aminocoumarins

Lisa Wirtz
a   Institut für Organische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany, Fax: +49(681)3022409   Email: u.kazmaier@mx.uni-saarland.de
,
Dagmar Auerbach
b   Biophysikalische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany
,
Gregor Jung
b   Biophysikalische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany
,
Uli Kazmaier*
a   Institut für Organische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany, Fax: +49(681)3022409   Email: u.kazmaier@mx.uni-saarland.de
› Author Affiliations
Further Information

Publication History

Received: 13 March 2012

Accepted after revision: 18 April 2012

Publication Date:
05 June 2012 (online)


Abstract

Pechmann condensation is a straightforward protocol for the synthesis of alkynyl- and azido-substituted 7-(dialkylamino)coumarins, which can be coupled to amino acid and peptide derivatives by copper-catalyzed [3+2]-cycloaddition (click reaction) in high yield. This allows the introduction of these efficient fluorescence labels into biologically relevant molecules.

Supporting Information

 
  • References

    • 1a Valeur B, Brochon J.-C. New Trends in Fluorescence Spectroscopy: Applications to Chemical and Life Sciences. Springer; Berlin: 2001
    • 1b Goldys EM. Fluorescence Applications in Biotechnology and Life Science. Wiley; Hoboken: 2009
    • 2a Hama Y, Urano Y, Koyama Y, Gunn AJ, Choyke PL, Kobayashi H. Clin. Cancer Res. 2007; 13: 6335
    • 2b Dillingham MS, Wallace MI. Org. Biomol. Chem. 2008; 6: 3031
    • 2c Neef AB, Schultz C. Angew. Chem. Int. Ed. 2009; 48: 1498 ; Angew. Chem. 2009, 121, 1526
    • 3a Sunahara H, Urano Y, Kojima H, Nagano T. J. Am. Chem. Soc. 2007; 129: 5597
    • 3b Ulrich G, Ziessel R, Harriman A. Angew. Chem. Int. Ed. 2008; 47: 1184 ; Angew. Chem. 2008, 120, 1202
    • 4a James TD, Sandanayake KR. A. S, Shinkai S. Angew. Chem. Int. Ed. 1994; 33: 2207 ; Angew. Chem. 1994, 106, 2287
    • 4b Ueno T, Urano Y, Setsukinai K.-I, Takakusa H, Kojima H, Kikuchi K, Ohkubo K, Fukuzumi S, Nagano T. J. Am. Chem. Soc. 2004; 126: 14079
  • 5 Maeda M. Laser Dyes. Academic Press; New York: 1984
  • 6 Yee DY, Balsanek V, Sames D. J. Am. Chem. Soc. 2004; 126: 2282
  • 7 Sletten EM, Bertozzi CR. Angew. Chem. Int. Ed. 2009; 48: 6974 ; Angew. Chem. 2009, 121, 7108
    • 8a Bernardes GJ. L, Chalker JM, Errey JC, Davis BG. J. Am. Chem. Soc. 2008; 130: 5052
    • 8b Dondoni A. Angew. Chem. Int. Ed. 2008; 47: 8995 ; Angew. Chem. 2008, 120, 9133
    • 8c Triola G, Brunsveld L, Waldmann H. J. Org. Chem. 2008; 73: 3646
    • 8d Wittrock S, Becker T, Kunz H. Angew. Chem. Int. Ed. 2007; 46: 5226 ; Angew. Chem. 2007, 119, 5319
    • 8e Jonkheijm P, Weinrich D, Köhn M, Engelkamp H, Christianen PC. M, Kuhlmann J, Maan JC, Nüsse D, Schröder H, Wacker R, Breinbauer R, Niemeyer CM, Waldmann H. Angew. Chem. Int. Ed. 2008; 47: 4421 ; Angew. Chem. 2008, 120, 4493
  • 9 McFarland JM, Francis MB. J. Am. Chem. Soc. 2005; 127: 13490
    • 10a Kodadek T, Duroux-Richard I, Bonnafous JC. Trends Pharmacol. Sci. 2005; 26: 210
    • 10b McFarland JM, Joshi NS, Francis MB. J. Am. Chem. Soc. 2008; 130: 7639
    • 10c Tilley SD, Francis MB. J. Am. Chem. Soc. 2006; 128: 1080
    • 11a Huisgen R. Angew. Chem., Int. Ed. Engl. 1963; 2: 565 ; Angew. Chem. 1963, 75, 604
    • 11b Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596 ; Angew. Chem. 2002, 114, 2708
    • 11c Tornoe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
    • 11d Chan TR, Hilgraf R, Sharpless KB, Fokin VV. Org. Lett. 2004; 6: 2853
    • 11e Rodionov VO, Presolski SI, Diaz DD, Fokin VV, Finn MG. J. Am. Chem. Soc. 2007; 129: 12705
  • 12 Sharpless KB, van der Eycken E. QSAR Comb. Sci. 2007; 26: 1110
  • 13 Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 20046 ; Angew. Chem. 2001, 113, 205
  • 14 Amo DS. D, Wang W, Jiang H, Besanceney C, Yan AC, Levy M, Liu Y, Marlow FL, Wu P. J. Am. Chem. Soc. 2010; 132: 16893
    • 15a Ullrich A, Chai Y, Pistorius D, Elnakady YA, Herrmann JE, Weissman KJ, Kazmaier U, Müller R. Angew. Chem. Int. Ed. 2009; 47: 4422 ; Angew. Chem. 2009, 121, 4486
    • 15b Ullrich A, Herrmann J, Müller R, Kazmaier U. Eur. J. Org. Chem. 2009; 6367
    • 15c Chai Y, Pistorius D, Ullrich A, Weissman KJ, Kazmaier U, Müller R. Chem. Biol. 2010; 17: 296
    • 15d Burkhart JL, Müller R, Kazmaier U. Eur. J. Org. Chem. 2011; 3050
  • 16 Burkhart JL, Kazmaier U. RSC Adv. 2012; in press
    • 17a v. Pechmann H. Ber. Dtsch. Chem. Ges. 1884; 17: 929
    • 17b Sethna SM, Phadke R. Org. React. 1953; 7: 1
  • 18 Wirtz L, Kazmaier U. Eur. J. Org. Chem. 2011; 7062
  • 19 Brooks DW, Lu LD. L, Masamune S. Angew. Chem., Int. Ed. Engl. 1979; 18: 72 ; Angew. Chem. 1979, 91, 76
  • 20 Alper PB, Hung S.-C, Wong C.-H. Tetrahedron Lett. 1996; 37: 6029
    • 21a Lundquist JT. IV, Pelletier JC. Org. Lett. 2001; 3: 781
    • 21b Ahsanullah Schmieder P, Kühne R, Rademann J. Angew. Chem. Int. Ed. 2009; 48: 5042 ; Angew. Chem. 2009, 121, 5143
  • 22 Klose J, Bienert M, Mollenkopf C, Wehle D, Zhang C.-W, Carpino LA, Henklein P. Chem. Commun. 1999; 1847
  • 23 Balog A, Curran DP. J. Org. Chem. 1995; 60: 337