Chemical ionization mass spectrometry of β lactam antibiotics

Article abstract of DOI:10.7164/antibiotics.28.668

Chemical ionization (CI) mass spectra are described for methyl esters of eight clinically significant penicillins and their breakdown products. These substances give spectra with very few fragment ions and contain easily discernible protonated molecule ions. The main cleavage reaction is postulated to involve a retro 2 + 2 Diels Alder type fragmentation of the β lactam ring liberating one fragment (m/e=174) that is characteristic of the penicillin nucleus and a second fragment that is molecule specific, as it contains the elements of the side chain. The other fragment ions, though interesting, are of minor intensity. The free acids, on the other hand, fragment more extensively because of their relative instability and lack of volatility. These spectra resemble electron impact spectra more closely and, though they encode more structural information, are less reproducible from run to run. The ease with which the esters can be made and the relative simplicity of their CI mass spectra make this method significant for the identification and characterization of β lactam antibiotics.