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Supramolecular Analysis of Monosaccharide Derivatives Using Cucurbit[7]uril and Electrospray Ionization Tandem Mass Spectrometry
Author(s) -
Lee Hyun Hee L.,
Kim Hugh I.
Publication year - 2018
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201700073
Subject(s) - chemistry , monosaccharide , tandem mass spectrometry , fragmentation (computing) , electrospray ionization , mass spectrometry , tandem , supramolecular chemistry , electrospray , computational chemistry , stereochemistry , molecule , organic chemistry , chromatography , materials science , composite material , computer science , operating system
Identification of monosaccharide derivatives using an analytical technique is difficult due to their isomeric structures and similar physical properties. Although mass spectrometry (MS) has emerged as a prominent technique for this purpose, a comprehensive MS‐based method for analyzing diverse monosaccharide species is yet to be developed. Herein, we employ host‐guest chemistry using cucurbit[7]uril (CB[7]) with MS to identify four different monosaccharide derivative species. Tandem MS analysis distinguishes the monosaccharide derivatives based on the unique fragmentation pattern produced when forming gas‐phase complexes with CB[7]. The ion mobility studies combined with computational calculations reveal that subtle differences in isomers cause distinct orientations inside CB[7] cavity, resulting in different fragmentation patterns of the isomers. This unique study demonstrates that host‐guest chemistry combined with MS can be used for developing effective isomer analysis techniques.