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J. Biol. Chem., Vol. 280, Issue 49, 40731-40748, December 9, 2005

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Identification and Characterization of Keyhole Limpet Hemocyanin N-Glycans Mediating Cross-reactivity with Schistosoma mansoni^*

Hildegard Geyer, Manfred Wuhrer, Anja Resemann¶, and Rudolf Geyer1

From the Institute of Biochemistry, Faculty of Medicine, University of Giessen, Friedrichstrasse 24, D-35392 Giessen, Germany, the Department of Parasitology, Center of Infectious Diseases, Leiden University Medical Center, P.O. Box 9600, NL-2300 RC Leiden, The Netherlands, and ^¶Bruker Daltonik GmbH, Fahrenheitstrasse 4, D-28359 Bremen, Germany

Keyhole limpet hemocyanin (KLH) of the mollusc Megathura crenulata is known to serologically cross-react with Schistosoma mansoni glycoconjugates in a carbohydrate-dependent manner. To elucidate the structural basis for this cross-reactivity, KLH glycans were released from tryptic glycopeptides and fluorescently labeled. Cross-reacting glycans were identified using a polyclonal antiserum reacting with soluble S. mansoni egg antigens, isolated by a three-dimensional fractionation scheme and analyzed by different mass spectrometric techniques as well as linkage analysis and exoglycosidase treatment. The results revealed that cross-reacting species comprise 4.5% of released glycans. They all represent novel types of N-glycans with a Fuc(1-3)GalNAc(1-4)[Fuc(1-3)]GlcNAc motif, which is known to occur also in schistosomal glycoconjugates. The tetrasaccharide unit is attached to the 3-linked antenna of a trimannosyl core, which can be further decorated by galactosyl residues, a xylose residue in 2-position of the central mannose and/or a fucose at the innermost N-acetylglucosamine. This study provides for the first time detailed structural data on the KLH carbohydrate entities responsible for cross-reactivity with glycoconjugates from S. mansoni.

Received for publication, June 1, 2005 , and in revised form, August 15, 2005.

^* This work was supported by the Deutsche Forschungsgemeinschaft (Grants SFB535 and Ge386/3). The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

The on-line version of this article (available at http://www.jbc.org) contains supplemental Table S1 and Figs. S1 and S2.

¹ To whom correspondence should be addressed. Tel.: 49-641-99-47400; Fax: 49-641-99-47409; E-mail: Rudolf.Geyer{at}biochemie.med.uni-giessen.de.

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