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Simple approach to derivatization of alcohols and phenols for the analysis by matrix(surface)‐assisted laser desorption/ionization time‐of‐flight mass spectrometry
Author(s) -
Borisov Roman S.,
Zhilyaev Dmitrii I.,
Polovkov Nikolai Yu.,
Zaikin Vladimir G.
Publication year - 2014
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.7008
Subject(s) - chemistry , derivatization , mass spectrometry , reagent , phenols , mass spectrum , butylamine , matrix assisted laser desorption/ionization , pyridine , desorption , organic chemistry , chromatography , amine gas treating , adsorption
RATIONALE Direct analysis of hydroxyl‐containing compounds by matrix‐assisted laser desorption/ionization (MALDI) mass spectrometry (MS) methods is not always possible due to the neutral character of analytes. The suggested fixed‐charge derivatization may increase the ionization efficiency for various alcohols and phenols in specific matrix‐ and surface‐activated LDI conditions. METHODS Aliphatic and steroid alcohols, as well as chlorophenols, were converted into various ammonioacetyl derivatives, containing a covalently bonded charged group, by reaction with bromoacetyl chloride and amine‐type compounds such as triethylamine, pyridine or quinoline. The derivatives are suitable for MALDI‐time‐of‐flight (TOF)MS analysis. RESULTS Triethylammoniumacetyl, pyridyliumacetyl and quinoliniumacetyl derivatives were prepared from aliphatic alcohols, some sterols and chlorinated phenols in one stage with quantitative yields. The derivatives produced characteristic MALDI and SALDI mass spectra. CONCLUSIONS The suggested derivatization approach for the modification of alcohols is simple and does not require any expensive reagents. The derivatives include a fixed charge and produce intense signals in MALDI (preferentially non‐acidic matrices) and matrix‐free SALDI (nanostructured target) conditions. Corresponding mass spectra are suitable for the determination of molecular mass and profiling of alcohols. Copyright © 2014 John Wiley & Sons, Ltd.