Open AccessDirect Experimental Characterization of Glycosyl Cations by Infrared Ion Spectroscopy
Author(s) -
Hidde Elferink,
Marion E. Severijnen,
Jonathan Martens,
Rens A. Mensink,
Giel Berden,
Jos Oomens,
Floris P. J. T. Rutjes,
Anouk M. Rijs,
Thomas J. Boltje
Publication year - 2018
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.8b01236
Subject(s) - chemistry , glycosyl , infrared spectroscopy , infrared multiphoton dissociation , oxocarbenium , mass spectrometry , dissociation (chemistry) , ion , infrared , tandem mass spectrometry , spectroscopy , reactivity (psychology) , photochemistry , reactive intermediate , analytical chemistry (journal) , computational chemistry , stereochemistry , catalysis , organic chemistry , physics , alternative medicine , chromatography , quantum mechanics , pathology , nucleophile , medicine , optics
Glycosyl cations are crucial intermediates formed during enzymatic and chemical glycosylation. The intrinsic high reactivity and short lifetime of these reaction intermediates make them very challenging to characterize using spectroscopic techniques. Herein, we report the use of collision induced dissociation tandem mass spectrometry to generate glycosyl cations in the gas phase followed by infrared ion spectroscopy using the FELIX infrared free electron laser. The experimentally observed IR spectra were compared to DFT calculated spectra enabling the detailed structural elucidation of elusive glycosyl oxocarbenium and dioxolenium ions.
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