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Photoreactivity of β- and γ-Lactams |
Sonia Vilariño Patiño 1, Moisés Canle L 1, Rory A. More O Ferrall 2, Arturo Santaballa 1 |
1. Universidade da Coruña (UDC), Alejandro de la Sota, Coruña 15008, Spain |
Abstract |
Lactam derivatives are among the most important groups of antibiotics. Some of these may undergo photo-initiated reactions, leading to a loss of antibiotic activity or to a modification of their chemical structure [1]. Thus, penicillin derivatives containing a β-lactam structure undergo UV-initiated ring opening of their thiazolidine moiety to yield an imine-thiolate anion. γ-lactams, reported to have substantial antibacterial properties [2], also undergo UV-initiated photodegradation. We have investigated the mechanisms of the photo-initiated processes for both groups of compounds, i.e.: β- and γ-lactams, including the photophysical processes originated from the initially-generated excited states and the photochemical processes leading to the observed photoproducts. The obtained results are presented here. [1] M. Canle, A. Lawley, E. C. McManus, R. A. More O'Ferrall, Pure Appl. Chem. 1996, 68, 813. [2] G. K. Kar, B. C. Roy, S. D. Adhikari, J. K. Ray, N. K. Brahma, Bioorg. Med. Chem. 1998, 6, 2397. |
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Presentation: poster at 18th Conference on Physical Organic Chemistry, Posters, by Sonia Vilariño PatiñoSee On-line Journal of 18th Conference on Physical Organic Chemistry Submitted: 2006-06-02 09:12 Revised: 2009-06-07 00:44 |