The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Table of contents


Chemical Compound Review

beta-Heparin     (2R,3S,4S,5R,6R)-6- [(2R,3R,4R,5S,6R)-3...

Synonyms: Desmin 370, CHEBI:58465, MF701, LS-59483, DS 435, ...
This record was replaced with 3032806.
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-methylol-5-sulfoxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid


Psychiatry related information on (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-methylol-5-sulfoxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid


High impact information on (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-methylol-5-sulfoxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid


Chemical compound and disease context of (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-methylol-5-sulfoxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid


Biological context of (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-methylol-5-sulfoxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

  • Therefore, only a limited picture of the functional role of active site residues in DS depolymerization was presented in previous structural studies [1].
  • In addition, the Arg-364 mutant had an altered product profile after exhaustive digestion of DS, suggesting a role for this residue in defining the substrate specificity of chondroitinase B [1].
  • Exogenous heparan/dermatan sulphate chains behave similarly as either potentiators or inhibitors of cell motility (depending upon the assay) [14].
  • During infection, proteoglycan degradation and release of dermatan sulphate may therefore represent a previously unknown virulence mechanism, which could serve as a target for novel antibacterial strategies [3].
  • The pharmacokinetics of MF 701 infusion are consistent with those previously described after i.v. bolus administration [15].

Anatomical context of (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-methylol-5-sulfoxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

  • In addition, transformed chondroblasts initiated the synthesis of HS and increased their synthesis of DS to levels that matched those of transformed fibroblasts [16].
  • In contrast, control chondroblasts synthesized very low levels of HA and DS, no HS, and very high levels of CS [16].
  • Biglycan and decorin are small chondroitin/dermatan sulphate proteoglycans in the extracellular matrix of connective tissue that belong to the family of structurally related proteoglycans called small leucine-rich repeat proteins [17].
  • These mutations lead to a deficiency of the glycosidase alpha-L-iduronidase (IDUA), which is required for the degradation of heparan sulphate and dermatan sulphate and thus the storage of these glycosaminoglycans in the lysosome [18].
  • Interestingly, although cell responsiveness to hepatocyte growth factor is not restored by exogenous heparan/dermatan sulphate chains, it is by an immobilised heparan sulphate proteoglycan substratum [14].

Associations of (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-methylol-5-sulfoxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid with other chemical compounds


Gene context of (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-methylol-5-sulfoxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid

  • Sequence analysis of the N-terminal 20 amino acid residues reveals the presence of a single site for the potential substitution of dermatan sulphate at residue 4 of DS-PGII and two such sites at residues 5 and 10 for DS-PGI [23].
  • Furthermore, the dermatan sulphate chains synthesized on the xyloside in TGF-beta-treated fibroblasts contained a larger proportion of D-glucuronosyl residues than those of the control [24].
  • All these effects can be strongly inhibited by the addition of an antibody to CD44, except CS6 and DS [25].
  • The disease is caused by the inability to degrade dermatan sulphate and heparan sulphate due to mutations in the iduronate-2-sulphatase gene (IDS) [26].
  • Additional experiments demonstrated that dermatan sulphate and disaccharides of the structure [DeltaUA(2S)-GalNAc(4,6S)], or sucroseoctasulphate, inhibited the degradation of LL-37 [27].

Analytical, diagnostic and therapeutic context of (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-methylol-5-sulfoxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid


  1. Biochemical characterization of the chondroitinase B active site. Pojasek, K., Raman, R., Kiley, P., Venkataraman, G., Sasisekharan, R. J. Biol. Chem. (2002) [Pubmed]
  2. Distribution of glycosaminoglycans in the intima of human aortas: changes in atherosclerosis and diabetes mellitus. Wasty, F., Alavi, M.Z., Moore, S. Diabetologia (1993) [Pubmed]
  3. Dermatan sulphate is released by proteinases of common pathogenic bacteria and inactivates antibacterial alpha-defensin. Schmidtchen, A., Frick, I.M., Björck, L. Mol. Microbiol. (2001) [Pubmed]
  4. Sulodexide in the treatment of intermittent claudication. Results of a randomized, double-blind, multicentre, placebo-controlled study. Coccheri, S., Scondotto, G., Agnelli, G., Palazzini, E., Zamboni, V. Eur. Heart J. (2002) [Pubmed]
  5. Deficiencies of fibrillin and decorin in fibroblast cultures of a patient with neonatal Marfan syndrome. Superti-Furga, A., Raghunath, M., Willems, P.J. J. Med. Genet. (1992) [Pubmed]
  6. Heparin injection into the adult rat hippocampus induces seizures in the absence of macroscopic abnormalities. Mudher, A.K., Mellanby, J., McMath, H., Perry, V.H., Greene, J.R. Neuroscience (1999) [Pubmed]
  7. Mammalian eyes and associated tissues contain molecules that are immunologically related to cartilage proteoglycan and link protein. Poole, A.R., Pidoux, I., Reiner, A., Cöster, L., Hassell, J.R. J. Cell Biol. (1982) [Pubmed]
  8. Fibrinogen inhibits the heparin cofactor II-mediated antithrombin activity of dermatan sulfate. Zammit, A., Dawes, J. Blood (1995) [Pubmed]
  9. Dermatan sulphate induces plasminogen activator release in the perfused rat hindquarters. Abbadini, M., Zhu, G.J., Maggi, A., Pangrazzi, J., Donati, M.B., Mussoni, L. Blood (1987) [Pubmed]
  10. Differential effects of glycosaminoglycans on neurite growth on laminin and L1 substrates. Dou, C.L., Levine, J.M. J. Neurosci. (1995) [Pubmed]
  11. Absence of decorin adversely influences tubulointerstitial fibrosis of the obstructed kidney by enhanced apoptosis and increased inflammatory reaction. Schaefer, L., Macakova, K., Raslik, I., Micegova, M., Gröne, H.J., Schönherr, E., Robenek, H., Echtermeyer, F.G., Grässel, S., Bruckner, P., Schaefer, R.M., Iozzo, R.V., Kresse, H. Am. J. Pathol. (2002) [Pubmed]
  12. Composition and distribution of glycosaminoglycans in cultures of human normal and malignant glial cells. Glimelius, B., Norling, B., Westermark, B., Wasteson, A. Biochem. J. (1978) [Pubmed]
  13. Biosynthesis of dermatan sulphate. Defructosylated Escherichia coli K4 capsular polysaccharide as a substrate for the D-glucuronyl C-5 epimerase, and an indication of a two-base reaction mechanism. Hannesson, H.H., Hagner-McWhirter, A., Tiedemann, K., Lindahl, U., Malmström, A. Biochem. J. (1996) [Pubmed]
  14. Differential regulation of hepatocyte growth factor/scatter factor by cell surface proteoglycans and free glycosaminoglycan chains. Deakin, J.A., Lyon, M. J. Cell. Sci. (1999) [Pubmed]
  15. Human pharmacokinetics and pharmacodynamics of MF 701 dermatan sulfate administered by continuous intravenous infusion. Agnelli, G., Cosmi, B., Renga, C., Federici, F., Nenci, G.G., Houin, G., Gianese, F. Thromb. Haemost. (1990) [Pubmed]
  16. Transformation by Rous sarcoma virus induces similar patterns of glycosaminoglycan synthesis in chick embryo skin fibroblasts and vertebral chondroblasts. Shanley, D.J., Cossu, G., Boettiger, D., Holtzer, H., Pacifici, M. J. Biol. Chem. (1983) [Pubmed]
  17. Biglycan and decorin induce morphological and cytoskeletal changes involving signalling by the small GTPases RhoA and Rac1 resulting in lung fibroblast migration. Tufvesson, E., Westergren-Thorsson, G. J. Cell. Sci. (2003) [Pubmed]
  18. Molecular genetics of mucopolysaccharidosis type I: diagnostic, clinical, and biological implications. Scott, H.S., Bunge, S., Gal, A., Clarke, L.A., Morris, C.P., Hopwood, J.J. Hum. Mutat. (1995) [Pubmed]
  19. Dermatan sulphate for the prevention of postoperative venous thromboembolism in patients with cancer. DOS (Dermatan sulphate in Oncologic Surgery) Study Group. Di Carlo, V., Agnelli, G., Prandoni, P., Coccheri, S., Gensini, G.F., Gianese, F., Mannucci, P.M. Thromb. Haemost. (1999) [Pubmed]
  20. Specific association of iduronic acid-rich dermatan sulphate with the extracellular matrix of human skin fibroblasts cultured on collagen gels. Gallagher, J.T., Gasiunas, N., Schor, S.L. Biochem. J. (1983) [Pubmed]
  21. Desmin 370, a low molecular weight dermatan sulfate, reduces the weight of preformed thrombi in rats made afibrinogenemic by ancrod. Barbanti, M., Calanni, F., Marchi, E., Semeraro, N., Colucci, M. Thromb. Haemost. (1995) [Pubmed]
  22. Trabecular meshwork glycosaminoglycans in human and cynomolgus monkey eye. Acott, T.S., Westcott, M., Passo, M.S., Van Buskirk, E.M. Invest. Ophthalmol. Vis. Sci. (1985) [Pubmed]
  23. Dermatan sulphate proteoglycans of human articular cartilage. The properties of dermatan sulphate proteoglycans I and II. Roughley, P.J., White, R.J. Biochem. J. (1989) [Pubmed]
  24. Transforming growth factor-beta induces selective increase of proteoglycan production and changes in the copolymeric structure of dermatan sulphate in human skin fibroblasts. Westergren-Thorsson, G., Schmidtchen, A., Särnstrand, B., Fransson, L.A., Malmström, A. Eur. J. Biochem. (1992) [Pubmed]
  25. Effect of sulfated GAGs on the expression and activation of MMP-2 and MMP-9 in corneal and dermal explant cultures. Isnard, N., Robert, L., Renard, G. Cell Biol. Int. (2003) [Pubmed]
  26. Mutation analysis of iduronate-2-sulphatase gene in 24 patients with Hunter syndrome: characterisation of 6 novel mutations. Mutation in brief no. 249. Online. Hartog, C., Fryer, A., Upadhyaya, M. Hum. Mutat. (1999) [Pubmed]
  27. Proteinases of common pathogenic bacteria degrade and inactivate the antibacterial peptide LL-37. Schmidtchen, A., Frick, I.M., Andersson, E., Tapper, H., Björck, L. Mol. Microbiol. (2002) [Pubmed]
  28. Proteolytic degradation of intestinal mucosal extracellular matrix after lamina propria T cell activation. Pender, S.L., Lionetti, P., Murch, S.H., Wathan, N., MacDonald, T.T. Gut (1996) [Pubmed]
  29. Modulation of collagen gel contraction by decorin. Bittner, K., Liszio, C., Blumberg, P., Schönherr, E., Kresse, H. Biochem. J. (1996) [Pubmed]
  30. Dermatan sulphate proteoglycans from sclera examined by rotary shadowing and electron microscopy. Ward, N.P., Scott, J.E., Cöster, L. Biochem. J. (1987) [Pubmed]
  31. A method for the sequence analysis of dermatan sulphate. Fransson, L.A., Havsmark, B., Silverberg, I. Biochem. J. (1990) [Pubmed]
  32. The absorption, clearance and metabolic fate of dermatan sulphate administered to man--studies using a radioiodinated derivative. Dawes, J., Hodson, B.A., Pepper, D.S. Thromb. Haemost. (1989) [Pubmed]
WikiGenes - Universities