Structural comparison of 1 beta-methylcarbapenem, carbapenem and penem: NMR studies and theoretical calculations.

T Nishimura, J Igarashi, A Sasaki, M Sunagawa

Research Center, Sumitomo Pharmaceuticals Co., Ltd., Osaka, Japan.

Bioorganic & medicinal chemistry 1998 Apr

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Structural comparisons of meropenem (1), desmethyl meropenem (2) and the penem analogue (3) which contain the same side chains at both C-2 and C-6 were performed using 1H NMR measurements together with 3-21G* level of ab initio MO and molecular mechanics calculations. The ab initio MO calculations reproduced the skeletons of these strained beta-lactam rings in good agreement with the crystallographic data. 1H NMR measurements in aqueous solution together with molecular modeling studies indicated that there were conformational differences of the C-2 and C-6 side chains in this series of compounds. These observations suggested that the conformational differences could affect their biological activities.

Citation

T Nishimura, J Igarashi, A Sasaki, M Sunagawa. Structural comparison of 1 beta-methylcarbapenem, carbapenem and penem: NMR studies and theoretical calculations. Bioorganic & medicinal chemistry. 1998 Apr;6(4):367-75