2,5-Dimethylphenacyl carbamate: A photoremovable protecting group for amines and amino acids

Photochemical and Photobiological Sciences

Volumn 6, Issue 1, 2007, Pages 50-56

  Kammari, Laxminarayana ^a   Plíštil, Lukáš ^a   Wirz, Jakob ^b   Klán, Petr ^a  

^a MASARYK UNIVERSITY   (Czech Republic)

^b UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIMETHYLPHENACYLCARBAMATE; ACETONITRILE; AMINE; AMINO ACID; ANILINE; CARBAMIC ACID DERIVATIVE; METHANOL; PHENYLALANINE METHYL ESTER; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOPHORE; DECARBOXYLATION; DEPROTECTION REACTION; LASER; LIGHT IRRADIANCE; PHOTOLYSIS; PHOTOREACTIVITY; PRIORITY JOURNAL; QUANTUM YIELD; SYNTHESIS; THERMOSTABILITY;

EID: 33846002030     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b612233g     Document Type: Article

References (38)

1. R. S. Givens, P. G. Conrad, A. L. Yousef and J.-I. Lee, in CRC Handbook of Organic Photochemistry and Photobiology, ed. W. M. Horspool and F. Lenci, CRC, Boca Raton, FL, 2004, ch. 69pp. 1–46.
2. A. P. Pelliccioli J. Wirz Photoremovable protecting groups: reaction mechanisms and applications Photochem. Photobiol. Sci. 2002 1 441-458.
3. C. G. Bochet Photolabile protecting groups and linkers J. Chem. Soc., Perkin Trans. 1 2002 125-142.
4. A. Patchornik B. Amit R. B. Woodward Photosensitive protecting groups J. Am. Chem. Soc. 1970 92 6333-6335.
5. C. G. Bochet Wavelength-selective cleavage of photolabile protecting groups Tetrahedron Lett. 2000 41 6341-6346.
6. J. F. Cameron C. G. Willson J. M. J. Frechet New photolabile amino protecting groups-photogeneration of amines from (3′,5′-dimethoxybenzoinyl)oxy carbonyl carbamates J. Chem. Soc., Chem. Commun. 1995 923-924.
7. J. F. Cameron C. G. Willson J. M. J. Frechet Photogeneration of amines from α-keto carbamates: Photochemical studies J. Am. Chem. Soc. 1996 118 12925-12937.
8. J. F. Cameron C. G. Wilson J. M. J. Frechet Photogeneration of amines from α-keto carbamates: Design and preparation of photoactive compounds J. Chem. Soc., Perkin Trans. 1 1997 2429-2442.
9. G. Papageorgiou J. E. T. Corrie Synthesis and properties of carbamoyl derivatives of photolabile benzoins Tetrahedron 1997 53 3917-3932.
10. M. C. Pirrung C. Y. Huang Photochemical deprotection of 3′,5′-dimethoxybenzoin (DMB) carbamates derived from secondary amines Tetrahedron Lett. 1995 36 5883-5884.
11. J. F. Cameron J. M. J. Frechet Photogeneration of organic bases from o-nitrobenzyl-derived carbamates J. Am. Chem. Soc. 1991 113 4303-4313.
12. J. E. Beecher J. F. Cameron J. M. J. Frechet Photogeneration of polymeric amines. Synthesis, photo-cross-linking and photoimaging of copolymers containing photoactive carbamate pendant groups J. Mater. Chem. 1992 2 811-816.
13. G. Bucher J. C. Scaiano R. Sinta G. Barclay J. Cameron Laser flash photolysis of carbamates derived from 9-fluorenone oxime J. Am. Chem. Soc. 1995 117 3848-3855.
14. T. Furuta S. S. H. Wang J. L. Dantzker T. M. Dore W. J. Bybee E. M. Callaway W. Denk R. Y. Tsien Brominated 7-hydroxycoumarin-4-ylmethyls: Photolabile protecting groups with biologically useful cross-sections for two photon photolysis Proc. Natl. Acad. Sci. U. S. A. 1999 96 1193-1200.
15. G. Papageorgiou A. Barth J. E. T. Corrie Flash photolytic release of alcohols from photolabile carbamates or carbonates is rate-limited by decarboxylation of the photoproduct Photochem. Photobiol. Sci. 2005 4 216-220.
16. P. Klan M. Zabadal D. Heger 2,5-Dimethylphenacyl as a new photoreleasable protecting group for carboxylic acids Org. Lett. 2000 2 1569-1571.
17. M. Zabadal A. P. Pelliccioli P. Klan J. Wirz 2,5-Dimethylphenacyl esters: A photoremovable protecting group for carboxylic acids J. Phys. Chem. A 2001 105 10329-10333.
18. P. Klan A. P. Pelliccioli T. Pospisil J. Wirz 2,5-Dimethylphenacyl esters: A photoremovable protecting group for phosphates and sulfonic acids Photochem. Photobiol. Sci. 2002 1 920-923.
19. J. Literak J. Wirz P. Klan 2,5-Dimethylphenacyl carbonates: A photoremovable protecting group for alcohols and phenols Photochem. Photobiol. Sci. 2005 4 43-46.
20. P. G. Sammes Photoenolization Tetrahedron 1976 32 405-422.
21. R. Haag J. Wirz P. J. Wagner The photoenolization of 2-methylacetophenone and related compounds Helv. Chim. Acta 1977 60 2595-2607.
22. P. J. Wagner C. P. Chen A rotation-controlled excited-state reaction. The photoenolization of ortho alkyl phenyl ketones J. Am. Chem. Soc. 1976 98 239-241.
23. H. B. Shi W. X. Hu Y. Q. Sun Preparation of chloroformates using bis(trichloromethyl) carbonate J. Chem. Res. Synop. 2004 708-709.
24. J. S. Yadav G. S. Reddy M. M. Reddy H. M. Meshram Zinc promoted simple and convenient synthesis of carbamates: An easy access for amino group protection Tetrahedron Lett. 1998 39 3259-3262.
25. P. J. Wagner I. E. Kochevar A. E. Kemppainen Type II photoprocesses of phenyl ketones. Procedures for determining meaningful quantum yields and triplet lifetimes J. Am. Chem. Soc. 1972 94 7489-7494.
26. A. P. Pelliccioli P. P. Klan M. Zabadal J. Wirz Photorelease of HCl from o-methylphenacyl chloride proceeds through the Z-xylylenol J. Am. Chem. Soc. 2001 123 7931-7932.
27. J. E. T. Corrie A. Desantis Y. Katayama K. Khodakhah J. B. Messenger D. C. Ogden D. R. Trentham Postsynaptic activation at the squid giant synapse by photolytic release of L-glutamate from a caged L-glutamate J. Physiol. (London) 1993 465 1-8.
28. A. Banerjee D. E. Falvey Protecting groups that can be removed through photochemical electron transfer: Mechanistic and product studies on photosensitized release of carboxylates from phenacyl esters J. Org. Chem. 1997 62 6245-6251.
29. A. Banerjee K. Lee Q. Yu A. G. Fang D. E. Falvey Protecting group release through photoinduced electron transfer: wavelength control through sensitized irradiation Tetrahedron Lett. 1998 39 4635-4638.
30. D. E. Falvey C. Sundararajan Photoremovable protecting groups based on electron transfer chemistry Photochem. Photobiol. Sci. 2004 3 831-838.
31. D. D. Tanner J. J. Chen L. Chen C. Luelo Fragmentation of substituted acetophenone and halobenzophenone ketyls-calibration of a mechanistic probe J. Am. Chem. Soc. 1991 113 8074-8081.
32. S. Campbell E. M. Marzluff M. T. Rodgers J. L. Beauchamp M. E. Rempe K. F. Schwinck D. L. Lichtenberger Proton affinities and photoelectron-spectra of phenylalanine and N-methylphenylalanine and N, N-dimethylphenylalanine-correlation of lone-pair ionization energies with proton affinities and implications for N-methylation as a method to effect site-specific protonation of peptides J. Am. Chem. Soc. 1994 116 5257-5264.
33. D. H. Aue H. M. Webb M. T. Bowers Quantitative proton affinities, ionization potentials, and hydrogen affinities of alkylamines J. Am. Chem. Soc. 1976 98 311-317.
34. I. Lee C. K. Kim B. C. Lee Theoretical studies on the acid-hydrolysis of methyl carbamate J. Comput. Chem. 1987 8 794-800.
35. S. L. Johnson D. L. Morrison Kinetics and mechanism of decarboxylation of N-arylcarbamates. Evidence for kinetically important zwitterionic carbamic acid species of short lifetime J. Am. Chem. Soc. 1972 94 1323-1334.
36. M. Ramseier P. Senn J. Wirz Photohydration of benzophenone in aqueous acid J. Phys. Chem. A 2003 107 3305-3315.
37. R. G. Zepp M. M. Gumz W. L. Miller H. Gao Photoreaction of valerophenone in aqueous solution J. Phys. Chem. A 1998 102 5716-5723.
38. A. Banerjee K. Lee D. E. Falvey Photoreleasable protecting groups based on electron transfer chemistry. Donor sensitized release of phenacyl groups from alcohols, phosphates and diacids Tetrahedron 1999 55 12699-12710.