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Why gamma-and deltaAre less Active than beta-Lactams ? An ab Initio Study

Dobrowolski J.

Polish Journal of Chemistry

2001

Vol. 75, nr 10

1277-1286

Ab initio calculations (HF/6-31G** and MP2/6-31G**) were performed to investigate the intramolecular hydrogen bonding in the model beta-,gamma-, and delta-lectam molecules and . It was found that the intramolecular (C=O)O-H...O=C hydrogen bond stabilizes much more the gamma_- and delta_-lactam fused ring systems than the _-lactam penicillin and cephalosporin-like systems. This observation suggests that gamma_- and delta_-lactams block themselves by the intramolecular hydrogen bond and therefore are less active toward receptor active site than beta_-lactams. It is also likely that this factor can discriminate the beta_-lactamase inhibitors.