
pmid: 6694069
5R,6R-Benzylpenicilloic acid was found to epimerize slowly in alkaline media to 5S,6R-benzylpenicilloic acid until equilibrium was established. Epimerization proceeded via the imine tautomer of penamaldic acid rather than the enamine form and was found to favor the 5S,6R-epimer at equilibrium. The conversion process was monitored using both reverse-phase high-performance liquid chromatography and NMR spectroscopy.
Chemistry, Magnetic Resonance Spectroscopy, Chemical Phenomena, Penicillin G, Spectrophotometry, Ultraviolet, Stereoisomerism, Hydrogen-Ion Concentration, Chromatography, High Pressure Liquid, Polarography
Chemistry, Magnetic Resonance Spectroscopy, Chemical Phenomena, Penicillin G, Spectrophotometry, Ultraviolet, Stereoisomerism, Hydrogen-Ion Concentration, Chromatography, High Pressure Liquid, Polarography
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