Preparation of Stable Isotope-Labeled 2-Nitrobenzaldehyde Derivatives of Four Metabolites of Nitrofuran Antibiotics and Their Comprehensive Characterization by UV, MS, and NMR Techniques

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• 作者：Thierry Delatour ; Eric Gremaud ; Pascal Mottier ; Janique Richoz ; Francia Arce Vera ; and Richard H. Stadler
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2003
• 出版时间：October 22, 2003
• 年：2003
• 卷：51
• 期：22
• 页码：6371 - 6379
• 全文大小：189K
• 年卷期：v.51,no.22(October 22, 2003)
• ISSN：1520-5118

文摘

A convenient method is presented for the preparation of the carbon-13-labeled 2-nitrobenzaldehydederivatives of the nitrofuran metabolites 3-amino-2-oxazolidinone (AOZ), semicarbazide (SC),1-aminohydantoin (AH), and 3-amino-5-morpholinomethyl-2-oxazolidinone (AMOZ), with the purposeof using them as internal standards for the quantification of trace levels of nitrofuran residues byliquid chromatography-tandem mass spectrometry in foods of animal origin. The synthesis encompasses the nitration of [1,2,3,4,5,6-¹³C₆]toluene prior to chromyl compound-mediated oxidation ofthe methyl group into the corresponding aldehyde. The four metabolites of nitrofuran antibiotics werederivatized independently with the resulting ring-labeled 2-nitrobenzaldehyde (NBA) to obtain thetarget compounds. Both the isotopically enriched and native substances were used to perform acomprehensive fragmentation study by electrospray ionization (ESI) collision-induced dissociation(CID) mass spectrometry (MS). Full characterization of the nitrofuran derivatives was accomplishedwith ultraviolet (UV) and exhaustive nuclear magnetic resonance (NMR) analysis. A major advantageof the described procedure is that it can be extended to the preparation of other carbon-13-labeledderivatives of metabolites of nitrofuran antibiotics.Keywords: Stable isotope; nitrofuran antibiotics; metabolites; 3-amino-2-oxazolidinone; semicarbazide;1-aminohydantoin; 3-amino-5-morpholinomethyl-2-oxazolidinone; synthesis; NMR; MS