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Issue 24, 2019
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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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Supplementary files

Article information


Submitted
16 Aug 2019
Accepted
24 Oct 2019
First published
24 Oct 2019

Analyst, 2019,144, 7220-7226
Article type
Paper
Author version available

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, 144, 7220
DOI: 10.1039/C9AN01584A

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