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Glycobiology Advance Access published online on June 10, 2003
Glycobiology, doi:10.1093/glycob/cwg086
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Submitted on November 15, 2002
Revised on May 22, 2003
Accepted on May 22, 2003

© 2003 Oxford University Press

ORIGINAL ARTICLES

Structural investigation of chondroitin/dermatan sulfate oligosaccharides from human skin fibroblast decorin

Alina Zamfir 1, Daniela G. Seidler 2, Hans Kresse 2, and Jasna Peter-Katalinic 3*

1 Institute for Medical Physics and Biophysics, Biomedical Analysis Department, University of Münster, Robert-Koch-Str. 31, D-48149, Münster, Germany; National Institute for Research and Development in Electrochemistry and Condensed Matter, Timisoara, Romania
2 Institute of Physiological Chemistry and Pathobiochemistry, University of Münster, Waldeyerstr. 15, D-48149, Münster, Germany
3 Institute for Medical Physics and Biophysics, Biomedical Analysis Department, University of Münster, Robert-Koch-Str. 31, D-48149, Münster, Germany

* To whom correspondence should be addressed. E-mail: jkp{at}uni-muenster.de.

Abstract

Hybrid chondroitin/dermatan sulfate (CS/DS) glycosaminoglycan chains, derived from decorin secreted by human skin fibroblasts, were shown to interact with FGF-2, as did oligosaccharides derived therefrom by chondroitin B lyase digestion. In a first attempt to identify the biologically active sequence a novel protocol for structural analysis of enzyme-resistant oligosaccharides larger than standard trisulfated hexasaccharides was developed. The method bases on capillary electrophoresis (CE) for separating oversulfated species in off-line combination with nanoelectrospray ionization quadrupole time-of-flight tandem mass spectrometry (nanoESI-QTOF-MS/MS) in the negative ion mode. Under optimized CE and ESI-MS conditions, up to 12-mer oligosaccharides with different degrees of sulfation were identified. A novel tandem MS protocol (CID-VE) was applied to elucidate the structure of a previously undescribed pentasulfated CS/DS hexasaccharide, {Delta}-4,5-IdoAGalNAc[GlcAGalNAc]2(5S). In this molecular species, detected as a triply charged ion at m/z 511.38, three sulfates are found in the IdoAGalNAcGlcA moiety offering two structural variants: one containing sulfated IdoA together with a disulfated GalNAc moiety, while in the other one both uronic acids, i.e. GlcA and IdoA, and the amino sugar each carry a sulfate ester group.


CS/DS oligosaccharides, decorin, oversulfation, ESI QTOF CID-VE mass spectrometry, capillary electrophoresis
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