Ethyl substituted coumarin-4-yl derivatives as photoremovable protecting groups for amino acids with improved stability for SPPS

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 241, Issue , 2012, Pages 52-57

  Weis, Simone ^a   Shafiq, Zahid ^a   Gropeanu, Radu A ^a   Del Campo, Aránzazu ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

Caged peptides; Coumarin; Photoremovable protecting group; Phototriggers

Indexed keywords

EID: 84862168322     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2012.05.014     Document Type: Article

References (27)

1. G.C.R. Ellis-Davies Caged compounds: photorelease technology for control of cellular chemistry and physiology Nature Methods 4 2007 619 628
2. M. Matsuzaki, T. Hayama, H. Kasai, and G.C.R. Ellis-Davies Two-photon uncaging of γ-aminobutyric acid in intact brain tissue Nature Chemical Biology 6 2010 255 257
3. E.M. Callaway, and R. Yuste Stimulating neurons with light Current Opinion in Neurobiology 12 2002 587 592
4. M.C. Pirrung How to make a DNA chip Angewandte Chemie International Edition 41 2002 1276 1289
5. A. del Campo, D. Boos, H.W. Spiess, and U. Jonas Surface modification with orthogonal photosensitive silanes for sequential chemical lithography and site-selective particle deposition Angewandte Chemie International Edition 44 2005 4707 4712
6. V. San Miguel-Arnanz, C.G. Bochet, and A. Del Campo Wavelength selective caged surfaces: how many functional levels are possible? Journal of the American Chemical Society 133 2011 5380 5388
7. M. Wirkner, J.M. Alonso, V. Maus, M. Salierno, T.T. Lee, A.J. Garcia, and A. del Campo Triggered cell release from materials using bioadhesive photocleavable linkers Advanced Materials 23 2011 3907 3910
8. A.M. Kloxin, A.M. Kasko, C.N. Salinas, and K.S. Anseth Photodegradable hydrogels for dynamic tuning of physical and chemical properties Science 324 2009 59 63
9. C.G. Bochet Photolabile protecting groups and linkers Journal of the Chemical Society - Perkin Transactions 1 2002 125 142
10. L. Fan, R.W. Lewis, G.P. Hess, and B. Ganem A new synthesis of caged GABA compounds for studying GABAA receptors Bioorganic and Medicinal Chemistry Letters 19 2009 3932 3933
11. D. Geißler, W. Kresse, B. Wiesner, J. Bendig, H. Kettenmann, and V. Hagen DMACM-caged adenosine nucleotides: ultrafast phototriggers for ATP, ADP, and AMP activated by long-wavelength irradiation ChemBioChem 4 2003 162 170
12. V. Hagen, J. Bendig, S. Frings, T. Eckardt, S. Helm, D. Reuter, and U.B. Kaupp Highly efficient ultrafast phototriggers for cAMP and cGMP by using long-wavelength UV/Vis-activation Angewandte Chemie International Edition 40 2001 1045 1048
13. M. Wirkner, S. Weis, V. San Miguel, M. Álvarez, R.A. Gropeanu, M. Salierno, A. Sartoris, R.E. Unger, C.J. Kirkpatrick, and A. del Campo Photoactivatable caged cyclic RGD peptide for triggering integrin binding and cell adhesion to surfaces ChemBioChem 12 2011 2623 2629
14. Y. Ohmuro-Matsuyama, and Y. Tatsu Photocontrolled cell adhesion on a surface functionalized with a caged arginine-glycine-aspartate peptide Angewandte Chemie International Edition 47 2008 7527 7529
15. A.Z. Suzuki, T. Watanabe, M. Kawamoto, K. Nishiyama, H. Yamashita, M. Ishii, M. Iwamura, and T. Furuta Coumarin-4-ylmethoxycarbonyls as phototriggers for alcohols and phenols Organic Letters 5 2003 4867 4870
16. 2, OH, and CO functions Journal of Organic Chemistry 75 2010 2790 2797
17. T. Furuta, S.S.-H. Wang, J.L. Dantzker, T.M. Dore, W.J. Bybee, E.M. Callaway, W. Denk, and R.Y. Tsien Brominated 7-hydroxycoumarin-4-ylmethyls: photolabile protecting groups with biologically useful cross-sections for two photon photolysis Proceedings of the National Academy of Sciences of the United States of America 96 1999 1193 1200
18. V.R. Shembekar, Y. Chen, B.K. Carpenter, and G.P. Hess A protecting group for carboxylic acids that can be photolyzed by visible light Biochemistry 44 2005 7107 7114
19. N. Kotzur, B. Briand, M. Beyermann, and V. Hagen Wavelength-selective photoactivatable protecting groups for thiols Journal of the American Chemical Society 131 2009 16927 16931
20. K. Ito, and J. Maruyama Studies on stable diazoalkanes as potential fluorogenic reagents. 1. 7-Substituted 4-diazomethylcoumarins Chemical and Pharmaceutical Bulletin 31 1983 3014 3023
21. R.O. Schonleber, J. Bendig, V. Hagen, and B. Giese Rapid photolytic release of cytidine 5-diphosphate from a coumarin derivative: a new tool for the investigation of ribonucleotide reductases Bioorganic and Medicinal Chemistry 10 2002 97 101
22. D.J. Yee, V. Balsanek, D. Sames, Ligands for aldoketoreductases, PCT Patent WO 2006/023821 A2 (2006).
23. V.R. Shembekar, Y. Chen, B.K. Carpenter, and G.P. Hess Coumarin-caged glycine that can be photolyzed within 3 μs by visible light Biochemistry 46 2007 5479 5484
24. M. Skwarczynski, M. Noguchi, S. Hirota, Y. Sohma, T. Kimura, Y. Hayashi, and Y. Kiso Development of first photoresponsive prodrug of paclitaxel Bioorganic and Medicinal Chemistry Letters 16 2006 4492 4496
25. J. Schaal, N. Kotzur, B. Dekowski, J. Quilitz, M. Klimakow, P. Wessig, and V. Hagen A novel photorearrangement of (coumarin-4-yl)methyl phenyl ethers Journal of Photochemistry and Photobiology A 208 2009 171 179
26. B.R. Schade, V. Hagen, R. Schmidt, R. Herbrich, E. Krause, T. Eckardt, and J.r. Bendig Deactivation behavior and excited-state properties of (coumarin-4-yl)methyl derivatives. 1. Photocleavage of (7-methoxycoumarin-4-yl) methyl-caged acids with fluorescence enhancement Journal of Organic Chemistry 64 1999 9109 9117
27. R. Schmidt, D. Geissler, V. Hagen, and J. Bendig Mechanism of photocleavage of (coumarin-4-yl)methyl esters Journal of Physical Chemistry A 111 2007 5768 5774