Assignment of the C-5 configuration of penicilloic acids

Penicilloates prepared by the method of Munro et al (1978) were examined by nuclear magnetic resonance spectroscopy and optical rotation to assign the configuration at C-5. The configuration was 5S for carbenicillin and ticarcillin penicilloates and 5R for the other seven penicilloates examined. The chemical shift and coupling constants of 5-H and 6-H showed consistent differences between the isomers and the optical rotation of the 5R-isomers is consistently more positive than that of the corresponding 5S-isomer.