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Chemical Compound Review

SureCN6404275     (2R,3S,4S,5R)-3,4,5,6- tetrahydroxyoxane-2...

Synonyms: CHEBI:47903, AC1L9AG2, C06472, 2073-35-0, L-Iduronic acid, ...
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High impact information on L-Iduronic acid


Biological context of L-Iduronic acid


Anatomical context of L-Iduronic acid


Associations of L-Iduronic acid with other chemical compounds


Gene context of L-Iduronic acid

  • On the other hand, when [35S]glycosaminoglycans formed from DSDS after incubation with [35S]PAPS and C6ST-1 were digested with chondroitinase ACII, a major part of the radioactivity was recovered in fractions larger than hexasaccharides, indicating that C6ST-1 transferred sulphate to the GalNAc residues located in the L-iduronic acid-rich region [12].
  • The epitope of 473HD, but not of CS-56 or MO-225, was eliminated from DSD-1-PG by digestion with chondroitinase B, suggesting the close association of L-iduronic acid with the 473HD epitope [13].
  • By contrast, an unusually large coupling between H-2 and H-3 of the sulfated L-iduronic acid residue suggests a greater departure from the 1C4 conformation of this residue. when present in the binding sequence to AT-III than in the regular sequences [14].
  • A substrate for direct measurement of L-iduronic acid 2-sulfate sulfatase [9].
  • The pentasaccharide containing L-iduronic acid as the sole hexuronic acid showed higher affinity for FGF-2 than the other pentasaccharides, where one hexuronic acid unit at least is D-glucuronic acid [15].

Analytical, diagnostic and therapeutic context of L-Iduronic acid


  1. Irreversible glucuronyl C5-epimerization in the biosynthesis of heparan sulfate. Hagner-McWhirter, A., Li, J.P., Oscarson, S., Lindahl, U. J. Biol. Chem. (2004) [Pubmed]
  2. Targeted disruption of a murine glucuronyl C5-epimerase gene results in heparan sulfate lacking L-iduronic acid and in neonatal lethality. Li, J.P., Gong, F., Hagner-McWhirter, A., Forsberg, E., Abrink, M., Kisilevsky, R., Zhang, X., Lindahl, U. J. Biol. Chem. (2003) [Pubmed]
  3. Presence of N-unsubstituted glucosamine units in native heparan sulfate revealed by a monoclonal antibody. van den Born, J., Gunnarsson, K., Bakker, M.A., Kjellén, L., Kusche-Gullberg, M., Maccarana, M., Berden, J.H., Lindahl, U. J. Biol. Chem. (1995) [Pubmed]
  4. Interaction of heparin cofactor II with biglycan and decorin. Whinna, H.C., Choi, H.U., Rosenberg, L.C., Church, F.C. J. Biol. Chem. (1993) [Pubmed]
  5. Biosynthesis of dermatan sulfate. I. Formation of L-iduronic acid residues. Malmström, A., Fransson, L.A. J. Biol. Chem. (1975) [Pubmed]
  6. N.m.r. spectroscopic observations related to the function of sulfate groups in heparin. Calcium binding vs. biological activity. Ayotte, L., Perlin, A.S. Carbohydr. Res. (1986) [Pubmed]
  7. Synthesis of a 3-deoxy-L-iduronic acid containing heparin pentasaccharide to probe the conformation of the antithrombin III binding sequence. Lei, P.S., Duchaussoy, P., Sizun, P., Mallet, J.M., Petitou, M., Sinaÿ, P. Bioorg. Med. Chem. (1998) [Pubmed]
  8. Biosynthesis of dermatan sulphate. Loss of C-5 hydrogen during conversion of D-glucuronate to L-iduronate. Malmström, A. Biochem. J. (1981) [Pubmed]
  9. A substrate for direct measurement of L-iduronic acid 2-sulfate sulfatase. Ginsberg, L.C., Di Ferrante, D.T., Di Ferrante, N. Carbohydr. Res. (1978) [Pubmed]
  10. The acid lability of the glycosidic bonds of L-iduronic acid residues in glycosaminoglycans. Conrad, H.E. Biochem. J. (1980) [Pubmed]
  11. Structural features in heparin which modulate specific biological activities mediated by basic fibroblast growth factor. Ishihara, M., Shaklee, P.N., Yang, Z., Liang, W., Wei, Z., Stack, R.J., Holme, K. Glycobiology (1994) [Pubmed]
  12. Chondroitin 4-sulphotransferase-1 and chondroitin 6-sulphotransferase-1 are affected differently by uronic acid residues neighbouring the acceptor GalNAc residues. Yamada, T., Ohtake, S., Sato, M., Habuchi, O. Biochem. J. (2004) [Pubmed]
  13. Structural characterization of the epitopes of the monoclonal antibodies 473HD, CS-56, and MO-225 specific for chondroitin sulfate D-type using the oligosaccharide library. Ito, Y., Hikino, M., Yajima, Y., Mikami, T., Sirko, S., von Holst, A., Faissner, A., Fukui, S., Sugahara, K. Glycobiology (2005) [Pubmed]
  14. Mono- and bidimensional 500 MHz 1H-NMR spectra of a synthetic pentasaccharide corresponding to the binding sequence of heparin to antithrombin-III: evidence for conformational peculiarity of the sulfated iduronate residue. Torri, G., Casu, B., Gatti, G., Petitou, M., Choay, J., Jacquinet, J.C., Sinaÿ, P. Biochem. Biophys. Res. Commun. (1985) [Pubmed]
  15. A synthetic heparan sulfate pentasaccharide, exclusively containing L-iduronic acid, displays higher affinity for FGF-2 than its D-glucuronic acid-containing isomers. Kovensky, J., Duchaussoy, P., Bono, F., Salmivirta, M., Sizun, P., Herbert, J.M., Petitou, M., Sinaÿ, P. Bioorg. Med. Chem. (1999) [Pubmed]
  16. Determination of iduronic acid and glucuronic acid in glycosaminoglycans after stoichiometric reduction and depolymerization using high-performance liquid chromatography and ultraviolet detection. Karamanos, N.K., Hjerpe, A., Tsegenidis, T., Engfeldt, B., Antonopoulos, C.A. Anal. Biochem. (1988) [Pubmed]
  17. Diagnostic methods for the determination of iduronic acid in oligosaccharides. Whitfield, D.M., Stojkovski, S., Pang, H., Baptista, J., Sarkar, B. Anal. Biochem. (1991) [Pubmed]
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