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首页> 外文期刊>Environmental Science & Technology: ES&T >Multiple Roles of Cu(II) in Catalyzing Hydrolysis and Oxidation of beta-Lactam Antibiotics
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Multiple Roles of Cu(II) in Catalyzing Hydrolysis and Oxidation of beta-Lactam Antibiotics

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摘要

The widely used beta-lactam antibiotics such as penicillins and cephalosporins are known to be susceptible to Cu-II-catalyzed hydrolysis at their four-membered beta-lactam ring. However, this study elucidates that Cu-II can in fact play multiple roles in promoting the hydrolysis and/or oxidation of beta-lactam antibiotics under environmental aquatic conditions (pH 5.0-9.0 and 22 degrees C), depending on beta-lactams' structural characteristics and solution pH. Most significantly, the beta-lactam antibiotics that contain a phenylglycine primary amine group on the side chain can undergo direct oxidation by Cu-II via this functional group. On the other hand, the beta-lactam ring of penicillins is susceptible to Cu-II-catalyzed hydrolysis, followed by oxidation of the hydrolysis product by Cu-II. In contrast, the beta-lactam ring of cephalosporins is susceptible to Cu-II-catalyzed hydrolysis only. Solution pH influences the Cu-II-promoted transformation by affecting the beta-lactam and Cu-II complexation through protonation/deprotonation of critical organic functional groups. When Cu-II acts as an oxidant to promote the transformation of beta-lactam antibiotics to yield Cu-I, the overall role of Cu-II appears catalytic if the reaction occurs under ambient atmospheric condition, due to quick oxidation of Cu-I by oxygen to regenerate Cu-II. Compared to earlier literature that largely assumed only the hydrolytic catalyst role of Cu-II in promoting degradation of beta-lactam antibiotics, the oxidative roles of Cu-II identified by this study mark important contributions to a more accurate mechanistic understanding.

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  • 来源
    《Environmental Science & Technology: ES&T》 |2016年第22期|12156-12165|共10页
  • 作者

    Chen Jiabin; Sun Peizhe; Zhang YaleiHuang Ching-Hua;

  • 作者单位

    Suzhou Univ Sci & Technol, Sch Environm Sci & Engn, Suzhou 215001, Peoples R China;

    Tongji Univ, Coll Environm Sci & Engn, Shanghai 200092, Peoples R China;

    Georgia Inst Technol, Sch Civil & Environm Engn, Atlanta, GA 30332 USA;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
  • 原文格式 PDF
  • 正文语种 英语
  • 中图分类 环境科学、安全科学;
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