Watkins Michael A, WeWora Danielle V, Li Sen, Winger Brian E, Kenttämaa Hilkka I
Department of Chemistry, Purdue University, West Lafayette, IN 47907-2038, USA.
Anal Chem. 2005 Aug 15;77(16):5311-6. doi: 10.1021/ac050324b.
A mass spectrometry method is presented for the identification of compounds that contain the primary N-oxide functional group. This method utilizes a gas-phase ion-molecule reaction with dimethyl disulfide that rapidly and selectively derivatizes the protonated primary N-oxide functional group in a mass spectrometer to yield an ionic reaction product (with 31 Da higher mass than that of the protonated molecule) that is diagnostic for the presence of a primary N-oxide functionality. A variety of protonated analytes containing different functional groups were tested in Fourier transform ion-cyclotron resonance and triple quadrupole mass spectrometers to probe the selectivity of the reaction. Only molecules containing the protonated primary N-oxide functional group yielded the diagnostic reaction product; all other protonated molecules gave protonated dimethyl disulfide or no reaction products. The feasibility of this method for compound screening was tested by examining six analytes with the same molecular formula but different atom connectivity. The one analyte that contained the primary N-oxide functional group was readily differentiated from the other analytes.
本文介绍了一种用于鉴定含有伯N-氧化物官能团化合物的质谱方法。该方法利用与二甲基二硫的气相离子-分子反应，在质谱仪中快速、选择性地将质子化的伯N-氧化物官能团衍生化，生成一种离子反应产物（质量比质子化分子高31 Da），该产物可用于诊断伯N-氧化物官能团的存在。在傅里叶变换离子回旋共振和三重四极杆质谱仪中对多种含有不同官能团的质子化分析物进行了测试，以探究该反应的选择性。只有含有质子化伯N-氧化物官能团的分子产生诊断反应产物；所有其他质子化分子产生质子化的二甲基二硫或无反应产物。通过检测六种具有相同分子式但原子连接性不同的分析物，测试了该方法用于化合物筛选的可行性。含有伯N-氧化物官能团的一种分析物很容易与其他分析物区分开来。
