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MetaCyc Compound: 2-O-sulfo-β-D-glucuronate

Synonyms: 2-O-sulfo-β-D-glucuronic acid, GlcA2S

Superclasses: an organosulfur compoundan organosulfate

The hexapyranosic form of D-glucuronate, β-D-glucuronate is found in the glycosaminoglycans chondroitin sulfate, dermatan sulfate, heparin, heparan sulfate and hyaluronan. It is sometimes sulfated at the second position to form 2-O-sulfo-β-D-glucuronate

Chemical Formula: C6H8O10S

Molecular Weight: 272.18 Daltons

Monoisotopic Molecular Weight: 273.99946723200003 Daltons

2-<i>O</i>-sulfo-β-D-glucuronate compound structure

SMILES: C1(O)(C(O)C(OS(=O)(=O)[O-])C(O)OC(C(=O)[O-])1)

InChI: InChI=1S/C6H10O10S/c7-1-2(8)4(16-17(12,13)14)6(11)15-3(1)5(9)10/h1-4,6-8,11H,(H,9,10)(H,12,13,14)/p-2/t1-,2-,3-,4+,6+/m0/s1


Unification Links: PubChem:46926086

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -260.67926Inferred by computational analysis [Latendresse13]

In Reactions of unknown directionality:

Not in pathways:
an alcohol + 3'-phosphoadenylyl-sulfate = adenosine 3',5'-bisphosphate + an organosulfate + H+

Created 28-Jul-2010 by Caspi R, SRI International


Casu89: Casu, B. (1989). "in Heparin: Chemical and Biological Properties, Clinical Applications." Lane, D. A., and Lindahl, U., Eds, pp 25-49, CRC Press, Boca Raton, FL.

Fraser97a: Fraser JR, Laurent TC, Laurent UB (1997). "Hyaluronan: its nature, distribution, functions and turnover." J Intern Med 242(1);27-33. PMID: 9260563

Gallagher01a: Gallagher JT (2001). "Heparan sulfate: growth control with a restricted sequence menu." J Clin Invest 108(3);357-61. PMID: 11489926

Gatti79: Gatti, G., Casu, B., Hamer, G. K., Pelin, A. S. (1979). Macromolecules 12:1001-1007.

Girish07: Girish KS, Kemparaju K (2007). "The magic glue hyaluronan and its eraser hyaluronidase: a biological overview." Life Sci 80(21);1921-43. PMID: 17408700

Hovingh70: Hovingh P, Linker A (1970). "The enzymatic degradation of heparin and heparitin sulfate. 3. Purification of a heparitinase and a heparinase from flavobacteria." J Biol Chem 245(22);6170-5. PMID: 5484472

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lindahl78: Lindahl U, Hook M (1978). "Glycosaminoglycans and their binding to biological macromolecules." Annu Rev Biochem 47;385-417. PMID: 354500

Murphy04: Murphy KJ, Merry CL, Lyon M, Thompson JE, Roberts IS, Gallagher JT (2004). "A new model for the domain structure of heparan sulfate based on the novel specificity of K5 lyase." J Biol Chem 279(26);27239-45. PMID: 15047699

Rosenberg97: Rosenberg RD, Shworak NW, Liu J, Schwartz JJ, Zhang L (1997). "Heparan sulfate proteoglycans of the cardiovascular system. Specific structures emerge but how is synthesis regulated?." J Clin Invest 99(9);2062-70. PMID: 9151776

Trowbridge02: Trowbridge JM, Gallo RL (2002). "Dermatan sulfate: new functions from an old glycosaminoglycan." Glycobiology 12(9);117R-25R. PMID: 12213784

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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