Utilisation of Gas-Phase Ion—Molecule Reactions for Differentiation between Phospho- and Sulfocarbohydrates

Author:

Piatkivskyi Andrii1,Pyatkivskyy Yuriy2,Hurt Matt3,Ryzhov Victor1

Affiliation:

1. Department of Chemistry and Biochemistry, and Center for Biochemical and Biophysical Studies, Northern Illinois University, DeKalb, Illinois 60115, USA

2. Waters Corporation, 34 Maple St, Milford, Massachusetts 01757, USA

3. Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, USA

Abstract

Gas-phase ion-molecule reactions of four boron-containing neutrals were explored as a means for differentiation between isobaric phospho- and sulfocarbohydrates. Phosphorylation and sulfation impose an addition of 80 Da to the molecular mass, so for low-resolution mass spectrometers compounds that have such modifications will appear at the same nominal mass-to-charge ( m/z) ratio. However, the ions of these isobaric species behave differently in ion–molecule reactions. All four evaluated neutral molecules [trimethyl borate (TMB), triethyl borate (TEB), diethylmethoxyborane (DEMB) and diisopropoxymethylborane (DIPMB)] proved to be reactive towards phosphorylated sugars and unreactive towards sulfated carbohydrates. In addition, TMB and TEB were found suitable for distinguishing positional isomers of phosphorylated carbohydrates, while reactions with DEMB and DIPMB were successful in differentiating phosphorylated, sulfated and unmodified deprotonated sugars. Similar reactions in the positive ion mode (alkali cationised) were found to be less conclusive.

Publisher

SAGE Publications

Subject

Spectroscopy,Atomic and Molecular Physics, and Optics,General Medicine

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