Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2014; 46(16): 2191-2200
DOI: 10.1055/s-0033-1338636
DOI: 10.1055/s-0033-1338636
paper
Clickable Coumarins as Fluorescent Labels for Amino Acids
Further Information
Publication History
Received: 20 March 2014
Accepted after revision: 11 April 2014
Publication Date:
13 May 2014 (online)
Abstract
Seven trifunctional conjugates of Fmoc-protected amino acids with alkynyloxy-substituted coumarins have been prepared and spectroscopically characterized. The coumarin core was either coupled to the α or side chain amino group. This design allows for the linear or branched elongation to peptides or peptidomimetics. The synthetic potential of the conjugates was demonstrated by copper-catalyzed [3+2] cycloadditions to orthogonally protected peptidomimetic products as well as a biotinylated fluorescent amino acid.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1a Lavis LD, Raines RT. ACS Chem. Biol. 2008; 3: 142
- 1b Wysocki LM, Lavis LD. Curr. Opin. Chem. Biol. 2011; 15: 752
- 1c Krueger AT, Imperiali B. ChemBioChem 2013; 14: 788
- 2a Fernandez-Carneado J, Giralt E. Tetrahedron Lett. 2004; 45: 6079
- 2b Stahl PJ, Cruz JC, Li Y, Yu SM, Hristova K. Anal. Biochem. 2012; 424: 137
- 3a Dufau I, Mazarguil H. Tetrahedron Lett. 2000; 41: 6063
- 3b Costa SP, Oliveira E, Lodeiro C, Raposo MM. Tetrahedron Lett. 2008; 49: 5258
- 3c Katritzky AR, Narindoshvili T. Org. Biomol. Chem. 2009; 7: 627
- 3d Esteves CI, Raposo MM, Costa SP. Tetrahedron 2010; 66: 7479
- 3e Xiang Z, Wang L. J. Org. Chem. 2011; 76: 6367
- 3f Speight LC, Muthusamy AK, Goldberg JM, Warner JB, Wissner RF, Willi TS, Woodman BF, Mehl RA, Petersson EJ. J. Am. Chem. Soc. 2013; 135: 18806
- 4a Berthelot T, Lain G, Latxague L, Deleris G. J. Fluoresc. 2004; 14: 671
- 4b Berthelot T, Talbot JC, Lain G, Deleris G, Latxague L. J. Pept. Sci. 2005; 11: 153
- 5a Hossain MA, Mihara H, Ueno A. J. Am. Chem. Soc. 2003; 125: 11178
- 5b Katritzky AR, Yoshioka M, Narindoshvili T, Chung A, Johnson JV. Org. Biomol. Chem. 2008; 6: 4582
- 5c Katritzky AR, Narindoshvili T, Angrish P. Synthesis 2008; 2013
- 5d Mehiri M, Jing B, Ringhoff D, Janout V, Cassimeris L, Regen SL. Bioconjugate Chem. 2008; 19: 1510
- 5e Orange C, Specht A, Puliti D, Sakr E, Furuta T, Winsorb B, Goeldner M. Chem. Commun. 2008; 1217
- 5f Cobos-Correa A, Trojanek JB, Diemer S, Mall MA, Schultz C. Nat. Chem. Biol. 2009; 5: 628
- 5g Wysocka M, Lesner A, Gruba N, Korkmaz B, Gauthier F, Kitamatsu M, Łęgowska A, Rolka K. Anal. Chem. 2012; 84: 7241
- 5h Kuru E, Hughes HV, Brown PJ, Hall E, Tekkam S, Cava F, de Pedro MA, Brun YV, VanNieuwenhze MS. Angew. Chem. Int. Ed. 2012; 51: 12519
- 5i Murase T, Yoshihara T, Yamada K, Tobita S. Bull. Chem. Soc. Jpn. 2013; 86: 510
- 6a Brun MP, Bischoff L, Garbay C. Angew. Chem. Int. Ed. 2004; 43: 3432
- 6b Paschalidou K, Neumann U, Gerhartz B, Tzougraki C. Biochem. J. 2004; 382: 1031
- 6c Mitra S, Barrios AM. Bioorg. Med. Chem. Lett. 2005; 15: 5142
- 6d Wang J, Xie J, Schultz PG. J. Am. Chem. Soc. 2006; 128: 8738
- 7 Agnes RS, Jernigan F, Shell JR, Sharma V, Lawrence DS. J. Am. Chem. Soc. 2010; 132: 6075
- 8a Elsinghorst PW, Härtig W, Goldhammer S, Grosche J, Gütschow M. Org. Biomol. Chem. 2009; 7: 3940
- 8b Wirtz L, Kazmaier U. Eur. J. Org. Chem. 2011; 7062
- 9a Yongzheng Y, Reymond JL. Mol. BioSyst. 2005; 1: 57
- 9b Shilin SV, Garazd MM, Khilya VP. Chem. Nat. Compd. 2008; 44: 301
- 9c Ottesen LK, Jaroszewski JW, Franzyk H. J. Org. Chem. 2010; 75: 4983
- 9d Jølck RI, Sun H, Berg RH, Andresen TL. Chem. Eur. J. 2011; 17: 3326
- 9e Furuta T, Manabe K, Teraoka A, Murakoshi K, Ohtsubo A, Suzuki A. Org. Lett. 2012; 14: 6182
- 10 Mertens MD, Schmitz J, Horn M, Furtmann N, Bajorath J, Mareš M, Gütschow M. ChemBioChem 2014; 15: 955
-
11a Meldal M, Tornoe CW. Chem. Rev. 2008; 108: 2952
- 11b Pedersen DS, Abell A. Eur. J. Org. Chem. 2011; 2399
- 12 For a review, see: Johansson H, Pedersen DS. Eur. J. Org. Chem. 2012; 4267
- 13a Simon M, Zangemeister-Wittke U, Plückthun A. Bioconjugate Chem. 2012; 23: 279
- 13b Sminia TJ, Pedersen DS. Synlett 2012; 23: 2643
- 13c Kim J, Seo MH, Lee S, Cho K, Yang A, Woo K, Kim HS, Park HS. Anal. Chem. 2013; 85: 1468
- 13d Nikić I, Plass T, Schraidt O, Szymański J, Briggs JA, Schultz C, Lemke EA. Angew. Chem. Int. Ed. 2014; 53: 2245
- 14 Wirtz L, Auerbach D, Jung G, Kazmaier U. Synthesis 2012; 44: 2005
- 15 Li C, Henry E, Mani NK, Tang J, Brochon JC, Deprez E, Xie J. Eur. J. Org. Chem. 2010; 2395
- 16 Mertens MD, Hinz S, Müller CE, Gütschow M. Bioorg. Med. Chem. 2014; 22: 1916
- 17 Mertens MD, Gütschow M. Chirality 2013; 25: 957
- 18 Mitsunobu O. Synthesis 1981; 1
- 19 Pendem N, Douat C, Claudon P, Laguerre M, Castano S, Desbat B, Cavagnat D, Ennifar E, Kauffmann B, Guichard G. J. Am. Chem. Soc. 2013; 135: 4884
- 20 Seefeld MA, Rouse MB, McNulty KC, Sun L, Wang J, Yamashit DS, Luengo JI, Zhang S, Minthorn EA, Concha NO, Heerding DA. Bioorg. Med. Chem. Lett. 2009; 19: 2244
- 21 Murata C, Masuda T, Kamochi Y, Todoroki K, Yoshida H, Nohta H, Yamaguchi M, Takadate A. Chem. Pharm. Bull. 2005; 53: 750
- 22 Akaji K, Aimoto S. Tetrahedron 2001; 57: 1749
- 23 Song A, Wang X, Lam KS. Tetrahedron Lett. 2003; 44: 1755
For reviews, see:
For reviews, see:
For recent examples, see: