Development of hydrophilic photolabile hydroxyl protecting groups

Photochemical and Photobiological Sciences

Volumn 11, Issue 3, 2012, Pages 514-517

  Yang, Haishen ^a   Zhou, Lei ^a   Wang, Pengfei ^a  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84863263167     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c1pp05281k     Document Type: Article

References (34)

1. V. N. R. Pillai Photoremovable protecting groups in organic synthesis Synthesis 1980 1
2. F. Guillier D. Orain M. Bradley Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry Chem. Rev. 2000 100 2091
3. A. P. Pelliccioli J. Wirz Photoremovable protecting groups: reaction mechanisms and applications Photochem. Photobiol. Sci. 2002 1 441
4. Dynamic studies in biology, ed., M. Goeldner, and, R. S. Givens, Wiley-VCH: Weinheim, Germany, 2005
5. G. Mayer A. Heckel Biologically active molecules with a "light switch" Angew. Chem., Int. Ed. 2006 45 4900
6. M. C. Pirrung Spatially addressable combinatorial libraries Chem. Rev. 1997 97 473
7. S. P. A. Fodor J. L. Read M. C. Pirrung L. Stryer A. T. Lu D. Solas Light-directed, spatially addressable parallel chemical synthesis Synthesis 1991 251 767
8. D. Woll S. Walbert K.-P. Stengele R. Green T. Albert W. Pfleiderer U. E. Steiner More efficient photolithographic synthesis of DNA-chips by photosensitization Nucleosides, Nucleotides Nucleic Acids 2003 22 1395
9. C. G. Bochet Photolabile protecting groups and linkers J. Chem,. Soc., Perkin Trans. 1 2002 125
10. C. G. Bochet;, A. Blanc, Photolabile protecting groups in organic synthesis, Handbook of Synthetic Photochemistry, ed., A. Albini, A. Fagnoni, Wiley-VCH, 2010, pp. 417-447
11. M. Goard G. Aakalu O. D. Fedoryak C. Quinonez J. St. Julien S. J. Poteet E. M. Schuman T. M. Dore Light-mediated inhibition of protein synthesis Chem. Biol. 2005 12 685
12. K. N. Plunkett A. Mohraz R. T. Haasch J. A. Lewis J. S. Moore Light-regulated electrostatic interactions in colloidal suspensions J. Am. Chem. Soc. 2005 127 14574
13. G. Han C.-C. You B.-J. Kim R. S. Turingan N. S. Forbes C. T. Martin V. M. Rotello Light-regulated release of DNA and its delivery to nuclei by means of photolabile gold nanoparticles Angew. Chem., Int. Ed. 2006 45 3165
14. M. A. Kostiainen D. K. Smith O. Ikkala Optically triggered release of DNA from multivalent dendrons by degrading and charge-switching multivalency Angew. Chem., Int. Ed. 2007 46 7600
15. D. D. Young A. Deiters Photochemical activation of protein expression in bacterial cells Angew. Chem., Int. Ed. 2007 46 4290
16. C. Park J. Lim M. Yun C. Kim Photoinduced release of guest molecules by supramolecular transformation of self-assembled aggregates derived from dendrons Angew. Chem., Int. Ed. 2008 47 2959
17. Y. Ohmuro-Matsuyama Y. Tatsu Photocontrolled cell adhesion on a surface functionalized with a caged arginine-glycine-aspartate peptide Angew. Chem., Int. Ed. 2008 47 7527
18. T. Muraoka C.-Y. Koh H. Cui S. I. Stupp Light-triggered bioactivity in three dimensions Angew. Chem., Int. Ed. 2009 48 5946
19. H. Yang X. Zhang L. Zhou P. Wang Development of a photolabile carbonyl-protecting group toolbox J. Org. Chem. 2011 76 2040
20. P. Wang M. Mondal Y. Wang Photolabile carbonyl protecting group: A new tool for light-controlled release of anticancer agents Eur. J. Org. Chem. 2009 2055
21. P. Wang Y. Wang H. Hu X. Liang Installation of photolabile carbonyl-protecting groups under neutral conditions without using any other chemical reagents Eur. J. Org. Chem. 2009 208
22. P. Wang Y. Wang H. Hu C. Spencer X. Liang L. Pan Sequential removal of photolabile protecting groups for carbonyls with controlled wavelength J. Org. Chem. 2008 73 6152
23. P. Wang H. Hu Y. Wang Application of the excited state meta effect in photolabile protecting group design Org. Lett. 2007 9 2831
24. P. Wang H. Hu Y. Wang Novel photolabile protecting group for carbonyl compounds Org. Lett. 2007 9 1533
25. L. Zhou H. Yang P. Wang Development of trityl-based photolabile hydroxyl protecting groups J. Org. Chem. 2011 76 5873
26. P. Wang L. Zhou X. Zhang X. Liang Facilitated photochemical cleavage of benzylic C-O bond. Application to photolabile hydroxyl-protecting group design Chem. Commun. 2010 46 1514
27. X. Huang R. Sreekumar J. Patel J. Walker Response of cardiac myocytes to a ramp increase of diacylglycerol generated by photolysis of a novel caged diacylglycerol Biophys. J. 1996 70 2448
28. R. Scott J. Pollock A. Ayar N. Thatcher U. Zehavi Synthesis and use of caged sphingolipids Methods Enzymol. 2000 312 387
29. K. Hayashi K. Hashimoto N. Kusaka A. Yamazoe H. Fukaki M. Tasaka H. Nozaki Caged gene-inducer spatially and temporally controls gene expression and plant development in transgenic Arabidopsis plant Bioorg. Med. Chem. Lett. 2006 16 2470
30. D. Gilbert K. Funk B. Dekowski R. Lechler S. Keller F. Mohrlen S. Frings V. Hagen Caged capsaicins: New tools for the examination of TRPV1 channels in somatosensory neurons ChemBioChem 2007 8 89
31. S. Cambridge D. Geissler F. Calegari K. Anastassiadis M. Hasan A. Stewart W. Huttner V. Hagen T. Bonhoeffer Doxycycline-dependent photoactivated gene expression in eukaryotic systems Nat. Methods 2009 6 527
32. A. Defoin R. Defoin-Straatmann K. Hildenbrand E. Bittersmann D. Kreft H. J. Kuhn A new liquid phase actinometer: quantum yield and photo-CIDNP study of phenylglyoxylic acid in aqueous solution J. Photochem. 1986 33 237
33. H. E. Zimmerman J. M. Nuss A. W. Tantillo Photochemistry. 152. Cyclopropanols and the di-π-methane rearrangement: mechanistic and exploratory organic photochemistry J. Org. Chem. 1988 53 3792
34. C.-T. Chen J.-H. Kuo V. D. Pawar Y. S. Munot S.-S. Weng C.-H. Ku C.-Y. Liu Nucleophilic acyl substitutions of anhydrides with protic nucleophiles catalyzed by amphoteric, oxomolybdenum species J. Org. Chem. 2005 70 1188