Direct monitoring of chemical transformations by combining thin layer chromatography with nanoparticle-assisted laser desorption/ionization mass spectrometry

A nanomaterial-assisted method that combines thin layer chromatography (TLC) with matrix-assisted laser desorption/ionization mass spectrometry (MALDI MS) was developed to directly monitor chemical transformations. A substrate-dependent extraction strategy was studied and successfully used to identi...

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Bibliographic Details
Published in:Analyst (London) 2013-03, Vol.138 (5), p.1379-1385
Main Authors: Chen, Chun-Chi, Yang, Yung-Lin, Ou, Chun-Lin, Chou, Chih-Hung, Liaw, Chih-Chuang, Lin, Po-Chiao
Format: Article
Language:English
Subjects:
4-Aminopyridine - analogs & derivatives
4-Aminopyridine - chemistry
Catalysis
Chromatography, Thin Layer - methods
Desorption
Enrichment
Ferns - chemistry
Flavonoids - analysis
Ionization
Monitors
Nanomaterials
Nanoparticles - chemistry
Nanostructure
Plant Extracts - analysis
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization - methods
Sulfonamides - chemistry
Thin layer chromatography
Transformations
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Summary:A nanomaterial-assisted method that combines thin layer chromatography (TLC) with matrix-assisted laser desorption/ionization mass spectrometry (MALDI MS) was developed to directly monitor chemical transformations. A substrate-dependent extraction strategy was studied and successfully used to identify target molecules from the depths of a developed TLC plate. By using this strategy, a hydrophobic sample of interest was enriched on the surface of the TLC plate in the presence of acetonitrile, in contrast to using water and methanol to identify hydrophilic samples. The successful enrichment of samples by specific solvents provided stable desorption/ionization efficiencies of compounds of interest and led to very good sensitivity near the attomole scale. The method was then used to monitor 4-dimethylaminopyridine (DMAP)-catalyzed acylation in preparation of bifunctional sulfonamides. The labile DMAP-acyl intermediate and final sulfonamide product were clearly identified on TLC plates without external purification or sample preparation. Furthermore, in combination with collision-induced dissociation (CID) to provide structural information, the technique was successfully used in the natural product discovery of anti-inflammatory flavonoids from Helminthostachys zeylanica, a traditional Chinese herb. The newly proposed method provides a very low background from silica supports or organic matrices in the low molecular weight range (100-1000 Da). The technique may greatly accelerate studies of metabolomics, drug discovery, and organic synthesis.
ISSN:0003-2654
1364-5528
DOI:10.1039/c2an36423a