1-(2-Aminoethyl)-3-methyl-1H-imidazol-3-ium tetrafluoroborate: synthesis and application in carbohydrate analysis

Abstract

Reductive alkylation of the carbonyl group of carbohydrates with fluorescence or ionizing labels is a prerequisite for the sensitive analysis of carbohydrates by chromatographic and mass spectrometric techniques. Herein, 1-(2-aminoethyl)-3-methyl-1H-imidazol-3-ium tetrafluoroborate ([MIEA][BF4]) was successfully synthesized using tert-butyl N-(2-bromoethyl)carbamate and N-methylimidazole as starting materials. MIEA+ was then investigated as a multifunctional oligosaccharide label for glycan profiling and identification using LC-ESI-ToF and by MALDI-ToF mass spectrometry. The reductive amination of this diazole with carbohydrates was exemplified by labeling N-glycans from the model glycoproteins horseradish peroxidase, RNase B, and bovine lactoferrin. The produced MIEA+ glycan profiles were comparable to the corresponding 2AB labeled glycan derivatives and showed improved ESI-MS ionization efficiency over the respective 2AB derivatives, with detection sensitivity in the low picomol to the high femtomol range.