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Characterization of Novel Hydrolysis Products of Carbapenems by Electrospray Ionization Mass Spectrometry

Characterization of Novel Hydrolysis Products of Carbapenems by Electrospray Ionization Mass Spectrometry

Cuirong Sun, Jianmei Wu, Yuanjiang Pan

Rapid Commun Mass Spectrom. 2009 Oct;23(19):3205-12.

PMID: 19718775

Abstract:

Carbapenems, including meropenem and imipenem, exhibit low stability against acid or base reagents. The fragmentation behavior of meropenem and its acid hydrolysis products was investigated by Fourier transform ion cyclotron resonance electrospray ionization tandem mass spectrometry and ion trap tandem multi-stage mass spectrometry in both positive and negative ion mode. Only one neutral loss of CO(2) was observed from the precursor ion to the MS(4) product ions for the acid hydrolysis product and this behavior did not correspond to that expected for the previously accepted 1-pyrroline or 2-pyrroline structure with two carbonyl acid units. The unknown product was then proposed to be 2-(4-(5-(dimethylcarbamoyl)pyrrolidin-3-ylthio)-5-imino-3-methyl-6-oxotetrahydro-2H-pyran-2-yl)-3-hydroxybutanoic acid on the basis of the multi-stage mass spectrometric and accurate mass data. A similar acid hydrolysis product of imipenem was also identified by mass spectrometry, confirming that these carbapenems had the same acid hydrolysis behavior. The proposed structures were further confirmed by NMR experiments.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS793630	3-(dimethylcarbamoyl)-5-fluorobenzeneboronic acid			Price

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