Simplified Synthesis of Isotopically Labeled 5,5-Dimethyl-pyrroline N-Oxide 英文参考文献.docVIP

Molecules 2011, 16, 8428-8436; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Simplified Synthesis of Isotopically Labeled 5,5-Dimethyl-pyrroline N-Oxide Fabian Leinisch 1,*, JinJie Jiang 1, Leesa J. Deterding 2 and Ronald P. Mason 1 1 Laboratory of Toxicology and Pharmacology, National Institute of Environmental Health Sciences, National Institutes of Health, 111 TW Alexander Drive, Research Triangle Park, NC 27709, USA 2 Laboratory of Structural Biology, National Institute of Environmental Health Sciences, National Institutes of Health, 111 TW Alexander Drive, Research Triangle Park, NC 27709, USA * Author to whom correspondence should be addressed; E-Mail: leinischf@; Tel.: +1-919-541-7574; Fax: +1-919-541-1043. Received: 25 July 2011; in revised form: 14 September 2011 / Accepted: 21 September 2011 / Published: 10 October 2011 Abstract: 5,5-Dimethylpyrroline N-oxide (15N) and 5,5-di(trideuteromethyl)pyrroline N-oxide were synthesized from the respective isotopically labeled 2-nitropropane analogs obtained from the reaction of sodium nitrate with 2-halopropanes. This facile, straightforward process allows synthesizing isotopically labeled DMPO analogs in a 4-step reaction without special equipment. Keywords: spin trap; isotopic labeling; DMPO 1. Introduction Nitrone spin traps such as the most commonly used 5,5-dimethylpyrroline N-oxide (DMPO) are important reagents for the detection of free radicals by means of ESR spin trapping [1]. For certain mass spectrometry experiments or to investigate the fidelity of spin trapping, it is helpful to use isotopically labeled spin traps. The di(trideuteromethyl) analog of DMPO with its mass shift of +6 compared to unlabeled DMPO can be used for dual spin-trapping mass spectrometry experiments. Here, spin traps labeled with stable isotopes (2H, 15N or 13C) are utilized to sim