Cationic Xylene Tag for Increasing Sensitivity in Mass Spectrometry
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- 作者：Poguang Wang ; Qi Zhang ; Yuanyuan Yao…
- 关键词：Derivatization ; Mass tag ; Cation ; Mass spectrometry ; DNA adducts ; Metabolomics
- 刊名：Journal of The American Society for Mass Spectrometry
- 出版年：2015
- 出版时间：October 2015
- 年：2015
- 卷：26
- 期：10
- 页码：1713-1721
- 全文大小：2,048 KB
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Qi Zhang (1)
Yuanyuan Yao (1)
Roger W. Giese (1)
1. Northeastern University, Boston, MA, 02115, USA - 刊物主题：Analytical Chemistry; Biotechnology; Organic Chemistry; Proteomics; Bioinformatics;
- 出版者：Springer US
- ISSN：1879-1123
文摘
N-(2-(Bromomethyl)benzyl)-N,N-diethylethanaminium bromide, that we designate as CAX-B (cationic xylyl-bromide), is presented as a derivatization reagent for increasing sensitivity in mass spectrometry. Because of its aryl bromomethyl moiety, CAX-B readily labels compounds having an active hydrogen. In part, a CAX-tagged analyte (CAX-analyte) can be very sensitive especially in a tandem mass spectrometer (both ESI and MALDI). This is because of facile formation of an analyte-characteristic first product ion (as a xylyl-based cation) from favorable loss of triethylamine as a neutral from the precursor ion. This loss is enhanced both by resonance stabilization of the xylyl cation, and by anchimeric assistance from the ortho hetero atom of the attached analyte. High intensity of a first product ion opens up the opportunity for a CAX-analyte to be additionally sensitive when it is prone to a secondary neutral loss from the analyte part. For example, we have derivatized and detected 160 amol of thymidine by CAX-tagging/LC-MALDI-TOF/TOF-MS in this way, where the two neutral losses are triethylamine and deoxyribose. Other analytes detected at the amol level as CAX derivatives (as diluted standards) include estradiol and some nucleobases. The tendency for analytes with multiple active hydrogens to label just once with CAX (an advantage) is illustrated by the conversion of bisphenol A to a single product even when excess CAX-B is present. A family of analogous reagents with a variety of reactivity groups is anticipated as a consequence of replacing the bromine atom of CAX-B with various functional groups.