Glucuronic acid
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| Glucuronic acid | |
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| IUPAC name | 3,4,5,6- tetrahydroxytetrahydropyran- 2-carboxylic acid |
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| MeSH | |
| SMILES | C1(C(C(OC(C1O)O)C(=O)O)O)O |
| Properties | |
| Molecular formula | C6H10O7 |
| Molar mass | 194.139 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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Glucuronic acid (from Greek γλυκερός - "sweet") is a carboxylic acid. Its structure is similar to that of glucose. However, glucuronic acid's sixth carbon is oxidized to a carboxylic acid. Its formula is C6H10O7.
The salts of glucuronic acid are known as glucuronates; the anion C6H9O7− is the glucuronate ion.
Glucuronic acid should not be confused with gluconic acid, a linear carboxylic acid resulting from the oxidation of a different carbon of glucose. Both Glucuronic Acid and Gluconic Acid are reported to be found in the fermented drink known as Kombucha. Glucuronic acid has been attributed with the mildly-alcoholic effect that drinking the tea has for some.
Functions
Glucuronidation
Glucuronic acid is highly soluble in water. In the animal body, glucuronic acid is often linked to substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids. These linkages involve O-glycosidic bonds, and this linkage process is known as glucuronidation.[1] Glucuronidation occurs mainly in the liver, although the enzyme responsible for its catalysis, UDP-glucuronyltransferase, has been found in all major body organs, e.g., heart, kidneys, adrenal gland, spleen, and thymus.[1] UDP-glucuronic acid (glucuronic acid linked via a glycosidic bond to uridine diphosphate) is an intermediate in the process and is formed in the liver.
The substances resulting from glucuronidation are known as glucuronides (or glucuronosides) and are typically much more water-soluble than the non-glucuronic acid-containing substance from which they were originally synthesised. The human body uses glucuronidation to make a large variety of substances more water-soluble, and, in this way, allow for their subsequent elimination from the body upon urination. Hormones may also be glucuronidated to allow for easier transport around the body. Pharmacists also commonly link drugs to glucuronic acid to allow for easier drug delivery.
Acyl glucuronidation
Acyl glucuronidation is an important metabolic pathway for fluoroquinolone antibiotics.
N-glucuronidation
Conformation
Glucuronidases
Glucuronidases are those enzymes that hydrolyze the glycosidic bond between glucuronic acid and some other compound.
References
Further reading
- Chiu SH, Huskey SW (1998). "Species differences in N-glucuronidation". Drug Metab. Dispos. 26 (9): 838-47. PMID 9733661.
- Kuehl GE, Murphy SE (2003). "N-glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP-glucuronosyltransferases". Drug Metab. Dispos. 31 (11): 1361-8. doi:10.1124/dmd.31.11.1361. PMID 14570768.
- Kuehl GE, Murphy SE (2003). "N-glucuronidation of trans-3'-hydroxycotinine by human liver microsomes". Chem. Res. Toxicol. 16 (12): 1502-6. doi:10.1021/tx034173o. PMID 14680362.
- Benowitz NL, Perez-Stable EJ, Fong I, Modin G, Herrera B, Jacob P (1999). "Ethnic differences in N-glucuronidation of nicotine and cotinine". J. Pharmacol. Exp. Ther. 291 (3): 1196-203. PMID 10565842.
- Mannfred A Hollinger, Introduction to Pharmacology, ISBN 0-415-28033-8
- Chang, K. M.; McManus, K.; Greene, J.; Byrd, G. D.; DeBethizy, J. D. Glucuronidation as a metabolic pathway for nicotine metabolism. 1991
- Coffman B.L., King C.D., Rios G.R. and Tephly T.R. The glucuronidation of opioids, other xenobiotics, and androgens by humande:Glucuronidierung
de:Glucuronsäure fr:Acide glucuronique he:חומצה גלוקורונית ja:グルクロン酸sl:Glukuronska kislina
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
