AI Article Synopsis
- 5R,6R-Benzylpenicilloic acid slowly converts to 5S,6R-benzylpenicilloic acid in alkaline conditions until reaching equilibrium.
- The epimerization occurs through the imine tautomer of penamaldic acid, not the enamine form.
- The conversion was tracked using reverse-phase high-performance liquid chromatography and NMR spectroscopy.
Article Abstract
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.
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| http://dx.doi.org/10.1002/jps.2600730135 | DOI Listing |
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