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Volume 272, Number 41, Issue of October 10, 1997 pp. 25608-25616
©1997 by The American Society for Biochemistry and Molecular Biology, Inc.

Fucosylation of Disaccharide Precursors of Sialyl Lewis^X Inhibit Selectin-mediated Cell Adhesion

(Received for publication, April 7, 1997, and in revised form, July 21, 1997)

Arun K. Sarkar , Katherine S. Rostand ^§ , Rakesh K. Jain ^¶ , Khushi L. Matta ^¶ and Jeffrey D. Esko

From the  Division of Cellular and Molecular Medicine, Glycobiology Program, UCSD Cancer Center, University of California, San Diego, La Jolla, California 92093-0687, the ^§ Department of Cell Biology, Schools of Medicine and Dentistry, University of Alabama at Birmingham, Birmingham, Alabama 35294, and the ^¶ Department of Gynecologic Oncology, Roswell Park Cancer Institute, Buffalo, New York 14263

We showed previously that HL-60 and F9 mouse embryonal carcinoma cells will take up and deblock peracetylated Gal1-4GlcNAc-O-naphthalenemethanol (Gal1-4GlcNAc-NM) and use the disaccharide as a primer of oligosaccharide chains (Sarkar, A. K., Fritz, T. A., Taylor, W. H., and Esko, J. D. (1995) Proc. Natl. Acad. Sci. U. S. A. 92, 3323-3327). We now report that another disaccharide, acetylated GlcNAc1-3Gal-naphthalenemethanol (GlcNAc1-3Gal-NM), has even greater potency and that both compounds will inhibit sialyl Lewis^X (sLe^x)-dependent cell adhesion. When fed to U937 cells, acetylated forms of Gal1-4GlcNAc-NM and GlcNAc1-3Gal-NM primed oligosaccharides in a dose-dependent manner. Analysis of compounds assembled on Gal1-4GlcNAc-NM showed only one product, namely Gal1-4(Fuc1-3)GlcNAc-NM. In contrast, GlcNAc1-3Gal-NM generated Gal1-4GlcNAc1-3Gal-NM, Gal1-4(Fuc1-3)GlcNAc1-3Gal-NM, NeuAc2-3Gal1-4GlcNAc1-3Gal-NM, and NeuAc2-3Gal1-4(Fuc1-3)GlcNAc1-3Gal-NM. Both compounds decreased the incorporation of [³H]fucose into cellular glycoconjugates, without affecting the incorporation of [³H]mannosamine, a precursor of sialic acid residues. Moreover, the overall extent of sialylation was not affected based on the reactivity of cells to fluorescein isothiocyanate-conjugated Maackia amurensis lectin. Priming inhibited expression of sLe^x on cell surface glycoconjugates, which reduced E-selectin-dependent cell adhesion to tumor necrosis factor--activated human umbilical vein endothelial cells. GlcNAc1-3Gal-NM and Gal1-4GlcNAc-NM represent starting points for making enzyme-specific, site-directed inhibitors of glycosyltransferases that could act in living cells.

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