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Chemical Compound Review

Xyloside     (3R,4S,5R)-oxane-2,3,4,5- tetrol

Synonyms: Xylomed, Xylo-Pfan, D-xylopentose, D-xylopyranose, Xylo-Pfan (TN), ...
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Disease relevance of D-xylose


High impact information on D-xylose

  • Endothelial cell adhesion and migration on fibrinogen were inhibited by both beta-d xyloside and after cleavage of chondroitin sulfate from the core protein by chondroitinase ABC [6].
  • First, a xyloside was used to inhibit proteoglycan biosynthesis; second, a variant of the AtT-20 cell line was isolated that synthesized little of the sulfated proteoglycan [7].
  • These data indicate that xyloside induces a dramatic imbalance in the de novo-synthesized PGs of cellular and extracellular compartments and that cellular accumulation of xylosylated (sulfated) PGs selectively alters the Golgi apparatus of the glomerular epithelial cell, the cell that actively synthesizes PGs [8].
  • In addition, focal alterations in collagen fibril packing, and a disruption of lamellar organization were observed in beta-D xyloside-treated corneas [9].
  • Corneal stromas were studied using histochemistry and electron microscopy after in ovo treatment with beta-D xyloside [9].

Chemical compound and disease context of D-xylose


Biological context of D-xylose


Anatomical context of D-xylose

  • The proteoglycans synthesized by cells in a culture maintained on xyloside until Day 8, and then switched to medium with no xyloside 1 h prior to labeling, were characteristic of those synthesized by normal mature Day 8 chondrocytes [15].
  • Recognition of influenza virus-infected cells by class II-restricted, virus-specific cytotoxic T lymphocytes was not diminished by the presence of xyloside in the effector phase of the cytotoxicity assay [16].
  • We have used isolated rat liver Golgi membranes to reconstitute the synthesis of sulfated glycosaminoglycans (GAGs) onto the membrane-permeable, external acceptor xyloside [17].
  • While over 60% of the 35S-labeled material from the blastocoel of normal mesenchyme blastulae is voided from a Sepharose CL-2B column run in a dissociative solvent, only 10% from xyloside treated embryos is voided [18].
  • Using [35S]sulfate to label xyloside-initiated GAG chains we find that transport of GAG chains from the trans-Golgi to the cell surface is 15-fold lower in matured oocytes than in immature oocytes [19].

Associations of D-xylose with other chemical compounds


Gene context of D-xylose

  • The obligatory involvement of xyloside-primed heparan sulfate in restoration of bFGF-receptor binding was also demonstrated by its sensitivity to heparinase treatment and by the lack of restoration activity in CHO cell mutants that lack enzymatic activities required to form the repeating disaccharide unit characteristic of heparan sulfate [24].
  • Treating cultured cells with xyloside, which interferes with glycosaminoglycan attachment to proteoglycans, also completely blocked their ability to incorporate tenascin-C into matrix fibrils [25].
  • The mRNA levels for the scavenger receptor A-II and the LDL receptor were not affected by NaClO3 or xyloside treatment [26].
  • The xyloside treatment did not reduce the mRNA levels for uPA, indicating that the effect was at the post-translational level [27].
  • The binding of 125I-labeled PF4 on treated cells was decreased, and xyloside treatment of cells abrogated the biologic activity of PF4 in a plasma clot culture system [28].

Analytical, diagnostic and therapeutic context of D-xylose


  1. Xyloside transport by XylP, a member of the galactoside-pentoside-hexuronide family. Heuberger, E.H., Smits, E., Poolman, B. J. Biol. Chem. (2001) [Pubmed]
  2. Identification of a novel glycosaminoglycan core-like molecule. II. Alpha-GalNAc-capped xylosides can be made by many cell types. Salimath, P.V., Spiro, R.C., Freeze, H.H. J. Biol. Chem. (1995) [Pubmed]
  3. Alpha- and beta-xylosides alter glycolipid synthesis in human melanoma and Chinese hamster ovary cells. Freeze, H.H., Sampath, D., Varki, A. J. Biol. Chem. (1993) [Pubmed]
  4. Xyloside-induced disruption of interphotoreceptor matrix proteoglycans results in retinal detachment. Lazarus, H.S., Hageman, G.S. Invest. Ophthalmol. Vis. Sci. (1992) [Pubmed]
  5. Tumor attenuation by 2(6-hydroxynaphthyl)-beta-D-xylopyranoside requires priming of heparan sulfate and nuclear targeting of the products. Mani, K., Belting, M., Ellervik, U., Falk, N., Svensson, G., Sandgren, S., Cheng, F., Fransson, L.A. Glycobiology (2004) [Pubmed]
  6. CD44-related chondroitin sulfate proteoglycan, a cell surface receptor implicated with tumor cell invasion, mediates endothelial cell migration on fibrinogen and invasion into a fibrin matrix. Henke, C.A., Roongta, U., Mickelson, D.J., Knutson, J.R., McCarthy, J.B. J. Clin. Invest. (1996) [Pubmed]
  7. Sorting and secretion of adrenocorticotropin in a pituitary tumor cell line after perturbation of the level of a secretory granule-specific proteoglycan. Burgess, T.L., Kelly, R.B. J. Cell Biol. (1984) [Pubmed]
  8. Xylosylated-proteoglycan-induced Golgi alterations. Kanwar, Y.S., Rosenzweig, L.J., Jakubowski, M.L. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  9. beta-D xyloside alters dermatan sulfate proteoglycan synthesis and the organization of the developing avian corneal stroma. Hahn, R.A., Birk, D.E. Development (1992) [Pubmed]
  10. Significance of different conjugate forms of bilirubin in the formation of pigment gallstones. Keida, Y., Nakano, T., Tabata, M., Shimizu, S., Nakayama, F. J. Gastroenterol. Hepatol. (1991) [Pubmed]
  11. Cell density-dependent expression of chondroitin sulfate proteoglycan in cultured human monocytes. Uhlin-Hansen, L., Kolset, S.O. J. Biol. Chem. (1988) [Pubmed]
  12. Dependence of sea urchin primary mesenchyme cell migration on xyloside- and sulfate-sensitive cell surface-associated components. Lane, M.C., Solursh, M. Dev. Biol. (1988) [Pubmed]
  13. Xyloside effects on in vitro hematopoiesis: functional and biochemical studies. Kirby, S.L., Bentley, S.A. J. Cell. Physiol. (1991) [Pubmed]
  14. The effects of beta-D-xyloside on the synthesis of proteoglycans by skeletal muscle: lack of effect on decorin and differential polymerization of core protein-bound and xyloside-linked chondroitin sulfate. Carrino, D.A., Caplan, A.I. Matrix Biol. (1994) [Pubmed]
  15. Effects of 4-methyl umbelliferyl-beta-D-xylopyranoside on chondrogenesis and proteoglycan synthesis in chick limb bud mesenchymal cell cultures. Lohmander, L.S., Hascall, V.C., Caplan, A.I. J. Biol. Chem. (1979) [Pubmed]
  16. Xyloside inhibits synthesis of the class II-associated chondroitin sulfate proteoglycan and antigen presentation events. Rosamond, S., Brown, L., Gomez, C., Braciale, T.J., Schwartz, B.D. J. Immunol. (1987) [Pubmed]
  17. In vitro synthesis of sulfated glycosaminoglycans coupled to inter-compartmental Golgi transport. Fernández, C.J., Warren, G. J. Biol. Chem. (1998) [Pubmed]
  18. Inhibition of cell migration in sea urchin embryos by beta-D-xyloside. Solursh, M., Mitchell, S.L., Katow, H. Dev. Biol. (1986) [Pubmed]
  19. The secretory pathway is blocked between the trans-Golgi and the plasma membrane during meiotic maturation in Xenopus oocytes. Leaf, D.S., Roberts, S.J., Gerhart, J.C., Moore, H.P. Dev. Biol. (1990) [Pubmed]
  20. Stimulation of synthesis of free chondroitin sulfate chains by beta-D-xylosides in cultured cells. Galligani, L., Hopwood, J., Schwartz, N.B., Dorfman, A. J. Biol. Chem. (1975) [Pubmed]
  21. Transfer of xylose to steroids by rabbit liver microsomes. Layne, D.S., Labow, R.S., Paquet, A., Williamson, D.G. Biochemistry (1976) [Pubmed]
  22. beta-D-xyloside-mediated alteration in the synthesis of basement membrane proteoglycan. Ledbetter, S.R., Hassell, J.R. Arch. Biochem. Biophys. (1986) [Pubmed]
  23. Inducible beta-xyloside permease as a constituent of the xylan-degrading enzyme system of the yeast Cryptococcus albidus. Krátký, Z., Biely, P. Eur. J. Biochem. (1980) [Pubmed]
  24. Heparan sulfate primed on beta-D-xylosides restores binding of basic fibroblast growth factor. Miao, H.Q., Fritz, T.A., Esko, J.D., Zimmermann, J., Yayon, A., Vlodavsky, I. J. Cell. Biochem. (1995) [Pubmed]
  25. Glycosaminoglycans modulate fibronectin matrix assembly and are essential for matrix incorporation of tenascin-C. Chung, C.Y., Erickson, H.P. J. Cell. Sci. (1997) [Pubmed]
  26. Proteoglycans in macrophages: characterization and possible role in the cellular uptake of lipoproteins. Halvorsen, B., Aas, U.K., Kulseth, M.A., Drevon, C.A., Christiansen, E.N., Kolset, S.O. Biochem. J. (1998) [Pubmed]
  27. Secretion of macrophage urokinase plasminogen activator is dependent on proteoglycans. Pejler, G., Winberg, J.O., Vuong, T.T., Henningsson, F., Uhlin-Hansen, L., Kimata, K., Kolset, S.O. Eur. J. Biochem. (2003) [Pubmed]
  28. Inhibitory effect of platelet factor 4 on human erythroleukemic cells is dependent on cell surface heparan sulfate. Maurer, A.M., Han, Z.C., Dhermy, D., Briere, J. J. Lab. Clin. Med. (1996) [Pubmed]
  29. alpha-N-acetylgalactosamine-capping of chondroitin sulfate core region oligosaccharides primed on xylosides. Miura, Y., Freeze, H.H. Glycobiology (1998) [Pubmed]
  30. Role of proteoglycan in the binding of low-density lipoprotein to cultured arterial smooth muscle cells. Horn-Brahimi, M.C., Breton, M., Berrou, E., Deudon, E., Picard, J. Artery (1988) [Pubmed]
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