Supramolecular Analysis of Monosaccharide Derivatives Using Cucurbit[7]uril and Electrospray Ionization Tandem Mass Spectrometry

Hyun Hee L. Lee, Hugh I. Kim

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)472-478
Number of pages7
JournalIsrael Journal of Chemistry
Volume58
Issue number3
DOIs
Publication statusPublished - 2018 Apr 1

Keywords

  • carbohydrates
  • host-guest systems
  • mass spectrometry
  • supramolecular chemistry

ASJC Scopus subject areas

  • Chemistry(all)

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