Self-consistent field-molecular orbital (SCF-MO) calculations and nuclear magnetic resonance measurements for fosfomycin and related compounds

In the present work, the mechanism of action of fosfomycin [(-)-(1R,2S)-(1,2-epoxypropyl)phosphonic acid] as an antibiotic agent is studied by "ab initio" quantum mechanical calculations and by 1H, 13C, and 31P NMR measurements. Attention is focused on the relative charge density and chemi...

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Bibliographic Details
Published in:	Journal of pharmaceutical sciences Vol. 76; no. 9; p. 753
Main Authors:	Smeyers, Y G, Herńandez Laguna, A, Romero-Sánchez, F J, Fernández-Ibañez, M, Galvez-Ruano, E, Arias-Pérez, S
Format:	Journal Article
Language:	English
Published:	United States 01-09-1987
Subjects:	Anti-Bacterial Agents - chemistry Fosfomycin - chemistry Hydrogen-Ion Concentration Magnetic Resonance Spectroscopy Molecular Conformation
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Summary:	In the present work, the mechanism of action of fosfomycin [(-)-(1R,2S)-(1,2-epoxypropyl)phosphonic acid] as an antibiotic agent is studied by "ab initio" quantum mechanical calculations and by 1H, 13C, and 31P NMR measurements. Attention is focused on the relative charge density and chemical shift of the C(2) atom of the epoxy ring, which seems to be closely related with the activity of this antibiotic. The theoretical results suggest that the sulfhydryl addition should be preceded by a necessary anchoring of the phosphonate moiety on a positive group of the receptor.
ISSN:	0022-3549
DOI:	10.1002/jps.2600760915