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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
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MetaCyc Compound: 2-O-sulfo-β-D-glucuronate

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

Superclasses: an organosulfur compound an organosulfate

Summary:
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

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

InChIKey: InChIKey=COJBCAMFZDFGFK-AZLKCVHYSA-L

Unification Links: PubChem:46926086

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

In Reactions of unknown directionality:

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

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


References

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.

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

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

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
Page generated by SRI International Pathway Tools version 18.5 on Sun Dec 28, 2014, BIOCYC14A.