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Zeleny, R; Altmann, F; Praznik, W.
(1999): Structural characterization of the N-linked oligosaccharides from tomato fruit.
Phytochemistry. 1999; 51(2):199-210

Abstract:: The primary structures of the N-linked oligosaccharides from tomato fruit (Lycopersicon esculentum) have been elucidated. For the isolation of the protein fraction, two procedures were employed alternatively: a low temperature acetone powder method and ammonium sulfate precipitation of the tomato extract. After peptic digestion, the glycopeptides were purified by cation-exchange chromatography; the oligosaccharides were released by N-glycosidase A and fluorescently labelled with 2-aminopyridine. Structural characterization was accomplished by means of two-dimensional HPLC in combination with exoglycosidase digestions and MALDI-TOF mass spectrometry. Two varieties as well as two stages of ripening were investigated. In all the samples, the same sixteen N-glycosidic structures were detected; the two most abundant glycans showed identical properties to those of the major N-linked oligosaccharides of horseradish peroxidase and pineapple stem bromelain, respectively and accounted for about 65-78% of the total glycan amount; oligomannosidic glycans occurred only in small quantities (3-9%). The majority of the N-glycans were beta 1,2-xylosylated and carried an alpha 1,3-fucose residue linked to the terminal N-acetylglucosamine. This structural element contributes to cross-reactions among non-related glycoproteins and has been shown to be an IgE-reactive determinant (Tretter, Altmann, Kubelka, Marz, & Becker, 1993). The presented study gives a possible structural explanation for reported immunological cross-reactivities between tomato and grass pollen extracts due to carbohydrate IgE epitopes (Petersen, Vieths, Aulepp, Schlaak, & Becker, 1996), thereby demonstrating the importance of the structural characterization of plant N-glycans for a more reliable interpretation of immunological data. (C) 1999 Elsevier Science Ltd. All rights reserved.
Authors BOKU Wien:: Altmann Friedrich; Praznik Werner
Find related publications in this database (using NML MeSH Indexing): Carbohydrate Conformation -; Carbohydrate Sequence -; Chromatography, High Pressure Liquid -; Glycopeptides - chemistry; Lycopersicon esculentum - chemistry; Molecular Sequence Data - chemistry; Oligosaccharides - chemistry; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization - chemistry
Find related publications in this database (Keywords): Lycopersicon esculentum; tomato; N-glycans; fucose; HPLC; MALDI-TOF