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Photoreactivity of β- and γ-Lactams

Sonia Vilariño Patiño 1Moisés Canle L 1Rory A. More O Ferrall 2Arturo Santaballa 1

1. Universidade da Coruña (UDC), Alejandro de la Sota, Coruña 15008, Spain
2. University College Dublin, Dublin, Ireland

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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Related papers

Presentation: poster at 18th Conference on Physical Organic Chemistry, Posters, by Sonia Vilariño Patiño
See On-line Journal of 18th Conference on Physical Organic Chemistry

Submitted: 2006-06-02 09:12
Revised:   2009-06-07 00:44