New Phototriggers: Extending the p-Hydroxyphenacyl π-π* Absorption Range

Organic Letters

Volumn 2, Issue 11, 2000, Pages 1545-1547

  Conrad II, Peter G ^a   Givens, Richard S ^a   Weber, Jörg F W ^a   Kandler, Karl ^a,b  

^a UNIVERSITY OF KANSAS   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; ACETOPHENONE DERIVATIVE; BICUCULLINE; GLUTAMIC ACID; ION CHANNEL;

ANIMAL; ARTICLE; CHEMISTRY; CYTOLOGY; DRUG EFFECT; ELECTRIC CONDUCTIVITY; ELECTRON; HIPPOCAMPUS; LIGHT; LUMINESCENCE; NERVE CELL; PHOTOLYSIS; PHYSIOLOGY; RADIATION EXPOSURE; RAT;

ACETOPHENONES; ANIMALS; BICUCULLINE; ELECTRIC CONDUCTIVITY; ELECTRONS; GAMMA-AMINOBUTYRIC ACID; GLUTAMIC ACID; HIPPOCAMPUS; ION CHANNELS; LIGHT; LUMINESCENT MEASUREMENTS; NEURONS; PHOTOLYSIS; RATS;

EID: 0034203977     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005856n     Document Type: Article

References (18)

1. For the previous paper, see: Givens, R. S.; Weber, J. F. W.; Conrad, P. G.; Orosz, G.; Donahue, S. L.; Thayer, S. A. J. Am. Chem. Soc. 2000, 122, 2687-2697.
2. (a) Givens, R. S.; Park, C.-H. Tetrahedron Lett. 1996, 37, 6259-6262.
3. (b) Park, C.-H.; Givens, R. S. J. Am. Chem. Soc. 1997, 119, 2453-2463.
4. Givens, R. S.; Jung, A. H.; Park, C.-H.; Weber, J. F. W.; Bartlett, W. J. Am. Chem. Soc. 1997, 119, 8369-8370.
5. Kandler, K.; Katz, L. C.; Kauer, J. A. Nature Neuro. 1998, 1, 114-118.
6. (a) Conrad, P. G.; Givens, R. S.; Hellrung, B.; Rajesh, C. S.; Ramkseier, M.; Wirz, J. Submitted for publication.
7. (b) See also refs 1 and 2.
8. Anderson, J. C.; Reese, C. B. Tetrahedron Lett. 1962, 1-4.
9. A recent report by Corrie and Wan (Zhang, K.; Corrie, J. E. T.; Munasinghe, V. R. N.; Wan, P. J. Am. Chem. Soc. 1999, 121, 5625-5632) suggested a singlet state rearrangement preceded by deprotonation. While we differ on the multiplicity of the reaction and even on the order of the events, we are in substantial agreement that deprotonation does precede the rearrangement (see ref 5).
10. Hatchard, C. G.; Parker, C. A. Proc. R. Soc. London A 1956, A220, 518.
11. 2O, see: Simons, J. P. Photochemistry and Spectroscopy; J. Wiley-Interscience: New York, 1971; pp 212-213.
12. See the following and references therein for examples of alternative photoinduced α-cleavage reactions of substituted acetophenones, for example: (a) Scaiano, J. C.; Netto-Ferreira, J. C. J. Photochem. 1986, 32, 253-259. (b) Sheehan, J. C.; Umezawa, K. J. Org. Chem. 1973, 38, 3771-3774. (c) Banerjee, A.; Falvey, D. E. J. Am. Chem. Soc. 1998, 120, 2965-2966.
13. See the following and references therein for examples of alternative photoinduced α-cleavage reactions of substituted acetophenones, for example: (a) Scaiano, J. C.; Netto-Ferreira, J. C. J. Photochem. 1986, 32, 253-259. (b) Sheehan, J. C.; Umezawa, K. J. Org. Chem. 1973, 38, 3771-3774. (c) Banerjee, A.; Falvey, D. E. J. Am. Chem. Soc. 1998, 120, 2965-2966.
14. See the following and references therein for examples of alternative photoinduced α-cleavage reactions of substituted acetophenones, for example: (a) Scaiano, J. C.; Netto-Ferreira, J. C. J. Photochem. 1986, 32, 253-259. (b) Sheehan, J. C.; Umezawa, K. J. Org. Chem. 1973, 38, 3771-3774. (c) Banerjee, A.; Falvey, D. E. J. Am. Chem. Soc. 1998, 120, 2965-2966.
15. Hartnett, K. A.; Stout, A. K.; Rajdev, S.; Rosenberg, P. A.; Reynolds, I. J.; Aiszeman, E. J. Neurochem. 1997, 68, 1836-1845.
16. The experimental apparatus and wavelength range are described elsewhere. Kandler, K.; Givens, R.; Katz, L. C. Photostimulation with Caged Glutamate (Chapter 27). In Imaging Neurons: A Laboratory Manual; Yuste, Lanni, R. F., Konnerth, A., Eds.; Cold Spring Harbor Laboratory Press: 1997. Typically, 2 ms UV flashes were employed.
17. Bicuculline is a known GABA A-receptor antagonist. The fact that the cell shows no response after the antagonist is added indicates that only free GABA causes the responses.
18. Givens, R. S.; Weber, J. F. W.; Jung, A. H.; Park, C.-H. New Photoprotecting Groups: Desyl and p-Hydroxyphenacyl Phosphate and Carboxylate Esters. In Methods in Enzymology: Caged Compounds; Marriott, G., Ed.; 1998, 291, 1-29.