p-Hydroxyphenacyl phototriggers: The reactive excited state of phosphate photorelease [26]

Journal of the American Chemical Society

Volumn 122, Issue 38, 2000, Pages 9346-9347

  Conrad II, Peter G ^b   Givens, Richard S ^b   Hellrung, Bruno ^a   Rajesh, Cheruvallil S ^a   Ramseier, Markus ^a   Wirz, Jakob ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

^b UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYPHENACYL DERIVATIVE; 4 HYDROXYPHENACYL DIETHYL PHOSPHATE; 4 HYDROXYPHENYLACETIC ACID; ACETONITRILE; FUNCTIONAL GROUP; PHOTOSENSITIZING AGENT; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; LETTER; PH; PHOSPHATE TRANSPORT; PHOTOLYSIS; PHOTOSENSITIZATION; PROTON TRANSPORT; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION;

EID: 0034721447     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001134f     Document Type: Letter

References (14)

1. Methods in Enzymology, Marriott, G., Ed.; Caged Compounds, Vol. 291; Academic Press: New York, 1998.
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7. Excimer laser operated on XeCl, 308 nm, ∼100 mJ per pulse, pulse width 25 ns. Low concentrations of ketones 1, 3, and 4 were used to avoid radical formation by intermolecular hydrogen abstraction: Das, P. K.; Encinas, M. V.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 4154-4162. Canonica, S.; Hellrung, B.; Wirz, J. J. Phys. Chem. A 2000, 104, 1226-1232.
8. Excimer laser operated on XeCl, 308 nm, ∼100 mJ per pulse, pulse width 25 ns. Low concentrations of ketones 1, 3, and 4 were used to avoid radical formation by intermolecular hydrogen abstraction: Das, P. K.; Encinas, M. V.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 4154-4162. Canonica, S.; Hellrung, B.; Wirz, J. J. Phys. Chem. A 2000, 104, 1226-1232.
9. max = 415 nm.
10. Spectrophotometric titration in tris(hydroxymethyl)amine/HCl buffer (ionic strength I = 0.1 M). See also: Vandenbelt, J. M.; Henrich, C.; Vandenberg, S. G. Anal. Chem. 1954, 26, 726-727.
11. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, revision B.2; Gaussian, Inc.: Pittsburgh, PA, 1995. B3LYP functionals (unrestricted for the triplet states) with the 6-31G* basis sel. Zero-point and thermal free-energy corrections were included. This method gives reliable values for keto-enol equilibria: Sklenák, S.; Apeloig, Y.; Rappoport, Z. J. Am. Chem. Soc. 1998, 120, 10359-10364.
12. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, revision B.2; Gaussian, Inc.: Pittsburgh, PA, 1995. B3LYP functionals (unrestricted for the triplet states) with the 6-31G* basis sel. Zero-point and thermal free-energy corrections were included. This method gives reliable values for keto-enol equilibria: Sklenák, S.; Apeloig, Y.; Rappoport, Z. J. Am. Chem. Soc. 1998, 120, 10359-10364.
13. 33 is quenched by oxygen (1 atm).
14. Ph = 0.79 s.