title: Self-consistent field-molecular orbital (SCF-MO) calculations and nuclear magnetic resonance measurements for fosfomycin and related compounds.
abstract: 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.
authors.affiliation: Instituto de Estructura de la Materia, C.S.I.C., Madrid, Spain.
authors.forename: Y G
authors.initials: YG
authors.lastname: Smeyers
authors.forename: A
authors.initials: A
authors.lastname: Herńandez Laguna
authors.forename: F J
authors.initials: FJ
authors.lastname: Romero-Sánchez
authors.forename: M
authors.initials: M
authors.lastname: Fernández-Ibañez
authors.forename: E
authors.initials: E
authors.lastname: Galvez-Ruano
authors.forename: S
authors.initials: S
authors.lastname: Arias-Pérez
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D005578:Fosfomycin / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation
chemical_list: D000900:Anti-Bacterial Agents; D005578:Fosfomycin