Selective Transformation of β-Lactam Antibiotics by Peroxymonosulfate: Reaction Kinetics and Nonradical Mechanism

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School of Environmental Science and Engineering, Suzhou University of Science and Technology, Suzhou 215009, P. R. China
School of Civil and Environmental Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332, United States
*Phone: 404-894-7694; Fax: 404-358-7087; E-mail: [email protected]
*Phone: +86 0512 68096895; Fax: +86 0512 68096895. Email: [email protected]
Cite this: Environ. Sci. Technol. 2018, 52, 3, 1461–1470
Publication Date (Web):January 2, 2018
https://doi.org/10.1021/acs.est.7b05543
Copyright © 2018 American Chemical Society
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Abstract

While the β-lactam antibiotics are known to be susceptible to oxidative degradation by sulfate radical (SO4•–), here we report that peroxymonosulfate (PMS) exhibits specific high reactivity toward β-lactam antibiotics without SO4•– generation for the first time. Apparent second-order reaction constants (k2,app) were determined for the reaction of PMS with three penicillins, five cephalosporins, two carbapenems, and several structurally related chemicals. The pH-dependency of k2,app could be well modeled based on species-specific reactions. On the basis of reaction kinetics, stoichiometry, and structure–activity assessment, the thioether sulfur, on the six- or five-membered rings (penicillins and cephalosporins) and the side chain (carbapenems), was the main reaction site for PMS oxidation. Cephalosporins were more reactive toward PMS than penicillins and carbapenems, and the presence of a phenylglycine side chain significantly enhanced cephalosporins’ reactivity toward PMS. Product analysis indicated oxidation of β-lactam antibiotics to two stereoisomeric sulfoxides. A radical scavenging study and electron paramagnetic resonance (EPR) technique confirmed lack of involvement of radical species (e.g., SO4•–). Thus, the PMS-induced oxidation of β-lactam antibiotics was proposed to proceed through a nonradical mechanism involving direct two-electron transfer along with the heterolytic cleavage of the PMS peroxide bond. The new findings of this study are important for elimination of β-lactam antibiotic contamination, because PMS exhibits specific high reactivity and suffers less interference from the water matrix than the radical process.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.est.7b05543.

  • Chemicals; chromatographic and MS conditions; EPR analysis; PMS determination; pH impact on PMS-induced oxidation of AMP and PG; transformation products of CFP; exclusion of 1O2 generation; tables and figures (PDF)

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