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Carbohydrate isomer resolution via multi-site derivatization cyclic ion mobility-mass spectrometry

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Abstract

Oligosaccharides serve many roles in extant life and may have had a significant role in prebiotic chemistry on the early Earth. In both these contexts, the structural and isomeric diversity among carbohydrates presents analytical challenges necessitating improved separations. Here, we showcase a chemical derivatization approach, where 3-carboxy-5-nitrophenylboronic acid (3C5NBA) is used to label vicinal hydroxyl groups, amplifying the structural difference between isomers. We explore the applicability of state-of-the-art ion mobility – mass spectrometry (IM-MS) instrumentation in the analysis of derivatized carbohydrates. In particular we focus on the resolving power required for IM separation of derivatized isomers. A recently developed cyclic ion mobility (cIM) mass spectrometer (MS) was chosen for this study as it allows for multi-pass IM separations, with variable resolving power (Rp). Three passes around the cIM (Rp ∼ 120) enabled separation of all possible pairs of four monosaccharide standards, and all but two pairs of eight disaccharide standards. Combining cIM methodology with tandem mass spectrometry (MS/MS) experiments allowed for the major products of each of the 3C5NBA carbohydrate derivatization reactions to be resolved and unequivocally identified.

Graphical abstract: Carbohydrate isomer resolution via multi-site derivatization cyclic ion mobility-mass spectrometry

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Publication details

The article was received on 16 Aug 2019, accepted on 24 Oct 2019 and first published on 24 Oct 2019


Article type: Paper
DOI: 10.1039/C9AN01584A
Analyst, 2019, Advance Article

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    Carbohydrate isomer resolution via multi-site derivatization cyclic ion mobility-mass spectrometry

    K. R. McKenna, L. Li, A. G. Baker, J. Ujma, R. Krishnamurthy, C. L. Liotta and F. M. Fernández, Analyst, 2019, Advance Article , DOI: 10.1039/C9AN01584A

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