N-Alkylpyridinium isotope quaternization for matrix-assisted laser desorption/ionization Fourier transform mass spectrometric analysis of cholesterol and fatty alcohols in human hair

Isotope-coded reagents have been developed for labeling of amino acids, phenols and fatty acids, but not for alcohols. In this work, a simple reaction based on direct N-alkylpyridinium isotope quaternization (NAPIQ) was developed for mild derivatization of cholesterol and fatty alcohols. Different f...

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Bibliographic Details
Published in:Analytica chimica acta 2011-03, Vol.690 (1), p.1-9
Main Authors: Wang, Hang, Wang, Haoyang, Zhang, Li, Zhang, Jing, Guo, Yinlong
Format: Article
Language:English
Subjects:
Alcoholic group
Alcohols
Analytical chemistry
Chemical derivatization
Chemistry
Cholesterol
Cholesterol - analysis
Exact sciences and technology
Fatty Alcohols - analysis
Fourier Analysis
Fourier transforms
Hair
Hair - chemistry
Humans
Ionization
Isotope Labeling
Isotope-coded reagent
Lasers
Marking
Mass spectrometry
Mesylates - chemistry
Pyridines
Pyridinium Compounds - chemistry
Pyridinium quaternization
Spectrometric and optical methods
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization - methods
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Summary:Isotope-coded reagents have been developed for labeling of amino acids, phenols and fatty acids, but not for alcohols. In this work, a simple reaction based on direct N-alkylpyridinium isotope quaternization (NAPIQ) was developed for mild derivatization of cholesterol and fatty alcohols. Different from the conventional quaternary reagents with cations on themselves, two simple and charge-neutral reagents: pyridine and d 5-pyridine directly attached N-cationic tag onto the target compounds in the presence of trifluoromethanesulfonic anhydride (Tf 2O) without tedious sample preparation. The derivatization completed in 5 min and achieved charge labeling of the target compounds, which significantly improved the detection limits of analytes by 10 3-folds in further analysis by matrix-assisted laser desorption/ionization Fourier transform mass spectrometry (MALDI–FTMS). The use of commercially available d 0/ d 5-pyridine pairs facilitated isotope-coded chemical derivatization and avoided the use of isotope-labeled internal standards; the excess pyridine did not affect the signals of analytes. Utility of the NAPIQ method was examined in the identification of cholesterol and fatty alcohols in small amount of human hair sample (
ISSN:0003-2670
1873-4324
DOI:10.1016/j.aca.2011.02.017