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- Title
Evaporative derivatization of phenols with 2-sulfobenzoic anhydride for detection by matrix-assisted laser desorption/ionization mass spectrometry.
- Authors
Yao, Yuanyuan; Wang, Poguang; Giese, Roger
- Abstract
RATIONALE Phenols are an important class of analytes, for example as bioactive environmental contaminants. Towards a goal of improving their detection by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) or MALDI-tandem time-of-flight (TOF/TOF)-MS, we studied their derivatization with 2-sulfobenzoic anhydride (SBA). We chose SBA for this purpose since it is commercially available, inexpensive, and forms an anionic derivative. METHODS Under the selected conditions developed here for phenols, a reaction mixture of one or more of such compounds in acetonitrile containing SBA and 4-dimethylaminopyridine (DMAP) is evaporated to a solid, heated at 60 °C for 1 h, redissolved in 50% acetonitrile containing matrix, spotted onto a MALDI target, and subjected to negative ion MALDI-TOF/TOF-MS. RESULTS While conventional (solution-phase) reaction of 4-phenylphenol (model analyte) with SBA and DMAP only gave a 47% yield of SBA-tagged 4-phenylphenol, evaporative derivatization as above gave a 96% yield, and 25 pmol (4.3 ng) of 4-phenylphenol could be detected in this way by MALDI-TOF/TOF-MS at signal-to-noise ratio (S/N) = 260, whereas even 1 nmol of the nonderivatized phenol was not detected in the absence of derivatization. A wide range of responses was observed when a mixture of 15 phenols was derivatized, with the higher responses coming from phenols with a p Ka value above 9. Without derivatization, phenols with p Ka values below 5 were the most readily detected. CONCLUSIONS Evaporative derivatization with SBA (a convenient reagent) can improve the detection of phenols with relatively high p Ka values (above 9) by negative ion MALDI-TOF-MS, and accomplish this in the absence of post-derivatization reaction cleanup. Copyright © 2014 John Wiley & Sons, Ltd.
- Subjects
PHENOLS; CHEMICAL reactions; DERIVATIZATION; AROMATIC compounds; ANTISEPTICS
- Publication
Rapid Communications in Mass Spectrometry: RCM, 2014, Vol 28, Issue 6, p653
- ISSN
0951-4198
- Publication type
Article
- DOI
10.1002/rcm.6816