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Chemical Compound Review

IDURONATE     (2S,3R,4R,5S)-2,3,4,5- tetrahydroxy-6-oxo...

Synonyms: L-iduronate, IDURONIC ACID, AG-F-15393, HMDB02704, CTK4H1633, ...
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Disease relevance of IDURONIC ACID


High impact information on IDURONIC ACID

  • These increases in enzyme activity were accompanied by corresponding increases in catabolism of heparan and dermatan sulfates, as shown by (a) a decrease in sulfate:uronic ratios of urinary oligosaccharides, (b) an increase in iduronic acid monosaccharide, and (c) a normalization of Bio-Gel P-2 gel filtration profiles [6].
  • Oversulfated disaccharides and nonconsecutive iduronic acid-containing units were the requirements for the E-CS/DS chains to bind PTN and to exhibit the neuritogenic activities [7].
  • In conclusion, we have selected an antibody that identifies HS oligosaccharides containing N-acetylated glucosamine and 2-O-sulfated iduronic acid residues [8].
  • D4ST-1 transfers sulfate to the C-4 hydroxyl of beta1,4-linked GalNAc that is substituted with an alpha-linked iduronic acid (IdoUA) at the C-3 hydroxyl [9].
  • Heparan sulfate oligomers showing a composition close to the dimeric repeats of heparin (glucosamine-NSO(3)(6-OSO(3))-iduronic acid(2-OSO(3))) n = 5 and n > 5, where iduronic acid may alternate with glucuronic acid, exhibit affinity for urokinase plasminogen activator and confer specificity on urokinase/urokinase receptor interaction [10].

Biological context of IDURONIC ACID

  • The minimal binding site is found in N-sulfated hexasaccharide domains and contains critical 2-O-sulfated iduronic acid residues [11].
  • Endocytosis and subsequent degradation of iduronic acid-rich small dermatan sulfate proteoglycan from fibroblast secretions were studied in human fibroblasts [12].
  • These elements, in addition to iduronic acid demonstrated previously (L. K. Hallak, P. L. Collins, W. Knudson, and M. E. Peeples, Virology 271:264-275, 2000), partially define cell surface molecules important for RSV infection of cultured cells [13].
  • The presence of C-6 sulphate ester on the non-reducing end 2-sulphaminoglucosamine stimulates sulphamate bond hydrolysis and substrate affinity if the adjacent monosaccharide residue is idose or 2-sulphoidose, but strongly inhibits hydrolysis if the adjacent monosaccharide residue is iduronic acid [14].
  • More precisely, we found a decrease in the iduronic acid content, associated with down-regulation of the 4-O-sulphation on the GalNAc residues [15].

Anatomical context of IDURONIC ACID

  • Heparan sulphate chains with a high degree of sulphation possessed also a significant number of iduronic acid residues and were isolated exclusively from porcine brain, liver and kidney medulla [16].
  • Consistent with the binding being a specific interaction, only iduronic acid-containing glycosaminoglycans inhibit the association of the 35S-labeled proteoglycan with calf brain membranes and facilitate the disassociation [17].

Associations of IDURONIC ACID with other chemical compounds


Gene context of IDURONIC ACID

  • Experiments with selectively desulfated heparins indicated that 2-O-sulfated iduronic acid units, in particular, are of importance to the interaction with HB-GAM, were implicated to a lesser extent [18].
  • Biglycan, but not decorin, from atherosclerotic plaque contained significantly reduced amounts of iduronic acid and disulfated disaccharides DeltaDi-2,4S and DeltaDi-4,6S relative to proteoglycan from normal artery [23].
  • The biglycan glycosaminoglycan chains were found to contain a similar ratio of 4-sulphate/6-sulphate, but with approx. 40-45% of the glucuronic acid epimerized to iduronic acid [24].
  • Thus, analogous proteoglycans from two different tissues, such as DS-PGI from skin and cartilage, possess a core protein with the same primary structure, yet contain glycosaminoglycan chains which differ greatly in iduronic acid content [25].
  • The findings showed that iduronic acid content is reduced by 50% in decorin and biglycan, whereas 4-O-sulfation is increased 2-fold in versican [26].

Analytical, diagnostic and therapeutic context of IDURONIC ACID


  1. Heparan sulfate undergoes specific structural changes during the progression from human colon adenoma to carcinoma in vitro. Jayson, G.C., Lyon, M., Paraskeva, C., Turnbull, J.E., Deakin, J.A., Gallagher, J.T. J. Biol. Chem. (1998) [Pubmed]
  2. Iduronic acid-containing glycosaminoglycans on target cells are required for efficient respiratory syncytial virus infection. Hallak, L.K., Collins, P.L., Knudson, W., Peeples, M.E. Virology (2000) [Pubmed]
  3. Structural characteristics of oversulfated chondroitin/dermatan sulfates in the fibrous lesions of the liver with cirrhosis. Koshiishi, I., Takenouchi, M., Imanari, T. Arch. Biochem. Biophys. (1999) [Pubmed]
  4. Pulsed amperometric detection of carbohydrates in lysosomal storage disease fibroblasts: a new screening technique for carbohydrate storage diseases. Blom, H.J., Andersson, H.C., Krasnewich, D.M., Gahl, W.A. J. Chromatogr. (1990) [Pubmed]
  5. Inseparable iduronic acid-containing proteoglycan PG(IdoA) preparations of human skin and post-burn scar tissues: evidence for elevated levels of PG(IdoA)-I in hypertrophic scar by N-terminal sequencing. Garg, H.G., Siebert, J.W., Garg, A., Neame, P.J. Carbohydr. Res. (1996) [Pubmed]
  6. Enzyme replacement therapy by fibroblast transplantation: long-term biochemical study in three cases of Hunter's syndrome. Dean, M.F., Stevens, R.L., Muir, H., Benson, P.F., Button, L.R., Anderson, R.L., Boylston, A., Mowbray, J. J. Clin. Invest. (1979) [Pubmed]
  7. Heparin-binding growth factor, pleiotrophin, mediates neuritogenic activity of embryonic pig brain-derived chondroitin sulfate/dermatan sulfate hybrid chains. Bao, X., Mikami, T., Yamada, S., Faissner, A., Muramatsu, T., Sugahara, K. J. Biol. Chem. (2005) [Pubmed]
  8. Detection of 2-O-sulfated iduronate and N-acetylglucosamine units in heparan sulfate by an antibody selected against acharan sulfate (IdoA2S-GlcNAc)n. ten Dam, G.B., van de Westerlo, E.M., Smetsers, T.F., Willemse, M., van Muijen, G.N., Merry, C.L., Gallagher, J.T., Kim, Y.S., van Kuppevelt, T.H. J. Biol. Chem. (2004) [Pubmed]
  9. Molecular cloning and characterization of a dermatan-specific N-acetylgalactosamine 4-O-sulfotransferase. Evers, M.R., Xia, G., Kang, H.G., Schachner, M., Baenziger, J.U. J. Biol. Chem. (2001) [Pubmed]
  10. Regulation of urokinase/urokinase receptor interaction by heparin-like glycosaminoglycans. Pucci, M., Fibbi, G., Magnelli, L., Del Rosso, M. J. Biol. Chem. (2001) [Pubmed]
  11. Common binding sites for beta-amyloid fibrils and fibroblast growth factor-2 in heparan sulfate from human cerebral cortex. Lindahl, B., Westling, C., Giménez-Gallego, G., Lindahl, U., Salmivirta, M. J. Biol. Chem. (1999) [Pubmed]
  12. Degradation of endocytosed dermatan sulfate proteoglycan in human fibroblasts. Hoppe, W., Rauch, U., Kresse, H. J. Biol. Chem. (1988) [Pubmed]
  13. Glycosaminoglycan sulfation requirements for respiratory syncytial virus infection. Hallak, L.K., Spillmann, D., Collins, P.L., Peeples, M.E. J. Virol. (2000) [Pubmed]
  14. Human liver sulphamate sulphohydrolase. Determinations of native protein and subunit Mr values and influence of substrate agylcone structure on catalytic properties. Freeman, C., Hopwood, J.J. Biochem. J. (1986) [Pubmed]
  15. Interferon gamma differentially affects the synthesis of chondroitin/dermatan sulphate and heparan sulphate by human skin fibroblasts. Praillet, C., Lortat-Jacob, H., Grimaud, J.A. Biochem. J. (1996) [Pubmed]
  16. Structural differences and the presence of unsubstituted amino groups in heparan sulphates from different tissues and species. Toida, T., Yoshida, H., Toyoda, H., Koshiishi, I., Imanari, T., Hileman, R.E., Fromm, J.R., Linhardt, R.J. Biochem. J. (1997) [Pubmed]
  17. Structural features and some binding properties of proteoheparan sulfate enzymatically labeled by calf brain microsomes. Miller, R.R., Waechter, C.J. Arch. Biochem. Biophys. (1984) [Pubmed]
  18. Neurite outgrowth in brain neurons induced by heparin-binding growth-associated molecule (HB-GAM) depends on the specific interaction of HB-GAM with heparan sulfate at the cell surface. Kinnunen, T., Raulo, E., Nolo, R., Maccarana, M., Lindahl, U., Rauvala, H. J. Biol. Chem. (1996) [Pubmed]
  19. Detection of glycosaminoglycans as a copper (II) complex in capillary electrophoresis. Toida, T., Linhardt, R.J. Electrophoresis (1996) [Pubmed]
  20. Partial characterization of dermatan sulfate by proton nuclear magnetic resonance spectroscopy. Longas, M.O. Anal. Biochem. (1990) [Pubmed]
  21. Analysis by high-performance liquid chromatography of radioactively labeled carbohydrate components of proteoglycans. Lohmander, L.S. Anal. Biochem. (1986) [Pubmed]
  22. Compositional and structural alterations of proteoglycans in human rectum carcinoma with special reference to versican and decorin. Tsara, M.E., Theocharis, A.D., Theocharis, D.A. Anticancer Res. (2002) [Pubmed]
  23. Altered dermatan sulfate structure and reduced heparin cofactor II-stimulating activity of biglycan and decorin from human atherosclerotic plaque. Shirk, R.A., Parthasarathy, N., San Antonio, J.D., Church, F.C., Wagner, W.D. J. Biol. Chem. (2000) [Pubmed]
  24. Immortalized, cloned mouse chondrocytic cells (MC615) produce three different matrix proteoglycans with core-protein-specific chondroitin/dermatan sulphate structures. Kokenyesi, R., Silbert, J.E. Biochem. J. (1997) [Pubmed]
  25. Characterization of the dermatan sulfate proteoglycans, DS-PGI and DS-PGII, from bovine articular cartilage and skin isolated by octyl-sepharose chromatography. Choi, H.U., Johnson, T.L., Pal, S., Tang, L.H., Rosenberg, L., Neame, P.J. J. Biol. Chem. (1989) [Pubmed]
  26. Regulation of the chondroitin/dermatan fine structure by transforming growth factor-beta1 through effects on polymer-modifying enzymes. Tiedemann, K., Olander, B., Eklund, E., Todorova, L., Bengtsson, M., Maccarana, M., Westergren-Thorsson, G., Malmström, A. Glycobiology (2005) [Pubmed]
  27. Inhibition of binding of malaria-infected erythrocytes by a tetradecasaccharide fraction from chondroitin sulfate A. Beeson, J.G., Chai, W., Rogerson, S.J., Lawson, A.M., Brown, G.V. Infect. Immun. (1998) [Pubmed]
  28. Biosynthesis and secretion of dermatan sulphate proteoglycans in cultures of human skin fibroblasts. Cöster, L., Carlstedt, I., Malmström, A., Särnstrand, B. Biochem. J. (1984) [Pubmed]
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