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Glycobiology Advance Access published online on October 26, 2009
Glycobiology, doi:10.1093/glycob/cwp169
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© The Author 2009. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oxfordjournals.org

HABA- based ionic liquid matrices for UV-MALDI-MS analysis of heparin and heparan sulfate oligosaccharides

C. Przybylski1,2, F. Gonnet1,2, D. Bonnaffé3, Y. Hersant3, H. Lortat-Jacob4 and R. Daniel1,2*

1 CNRS UMR 8587, Laboratoire Analyse et Modélisation pour la Biologie et l’Environnement, F-91025 Evry, France
2 Université d’Evry-Val-d’Essonne, Laboratoire Analyse et Modélisation pour la Biologie et l’Environnement, F-91025 Evry, France
3 Université Paris Sud 11, Institut de Chimie Moléculaire et des Matériaux CNRS UMR 8182, Laboratoire de Chimie Organique Multifonctionnelle, F-91405 Orsay Cedex, France
4 CEA-CNRS-UJF UMR 5075, Institut de Biologie Structurale, 38027 Grenoble Cedex, France

* To whom correspondence should be addressed. Fax: +33-1-69-47-7655. E-mail: regis.daniel{at}univ-evry.fr

Received on August 3, 2009; accepted on October 20, 2009

Polysulfated carbohydrates such as heparin (HP) and heparan sulfate (HS) are not easily amenable to usual ultraviolet matrix-assisted laser desorption/ionization-mass spectrometry (UV-MALDI)-MS analysis due to the thermal lability of their O- and N-SO3 moieties, and their poor ionization efficiency with common crystalline matrices. Recently, ionic liquid matrices showed considerable advantages over conventional matrices for MALDI-MS of acidic compounds. Two new ionic liquid matrices (ILMs) based on the combination of 2-(4-hydroxyphenylazo)benzoic acid (HABA) with 1,1,3,3-tetramethylguanidine and spermine were evaluated in the study herein. Both ILMs were successfully applied to the analysis of synthetic heparin oligosaccharides of well-characterized structures as well as to heparan sulfate derived oligosaccharides from enzymatic depolymerization. HABA-based ILMs showed improved signal-to-noise ratio as well as a decrease of fragmentation/desulfation processes and cation exchange. Sulfated oligosaccharides were detected with higher sensitivity than with usual crystalline matrices, and their intact fully O- and N-sulfated species [M-Na]– were easily observed on mass spectra. MALDI-MS characterization of analytes as much as challenging than heparin octasaccharide carrying 8-O and 4 N-sulfo groups, and heparin octadecasulfated dodecasaccharide were successfully achieved.


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