関: glucuronate、glucuronic、sodium glucuronate

WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/12/28 15:58:45」(JST)

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Glucuronic acid (from Ancient Greek γλυκύς "sweet" + οὖρον "urine") 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 and esters 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.

Functions

Proteoglycans

Glucuronic acid is common in carbohydrate chains of proteoglycans. It is part of mucous animal secretions (such as saliva), cell glycocalyx, and intercellular matrix (for instance hyaluronan).

Glucuronidation of toxic substances

In the animal body, glucuronic acid is often linked to the xenobiotic metabolism of substances such as drugs, pollutants, bilirubin, androgens, estrogens, mineralocorticoids, glucocorticoids, fatty acid derivatives, retinoids, and bile acids. These linkages involve glycosidic bonds, and this linkage process is known as glucuronidation.^[2] 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., intestine, kidneys, brain, adrenal gland, spleen, and thymus.^[3]^[4]

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 through urine or faeces (via bile from the liver). Hormones may also be glucuronidated to allow for easier transport around the body. Pharmacologists have linked drugs to glucuronic acid to allow for more effective delivery of a broad range of substances. Sometimes toxic substances are also less toxic after glucuronidation.

The conjugation of xenobiotic molecules with hydrophilic molecular species such as glucuronic acid is known as phase II metabolism.

The β-D methyl glycoside of glucuronic acid in the low energy ⁴C₁ conformation

Use

Determination of urinary steroids and of steroid conjugates in blood.

Both glucuronic acid and gluconic acid are reported to be contained in some commercially available brands of Kombucha.^[5]

In all plants and mammals-other than guinea pigs and primates-glucuronic acid is a precursor of ascorbic acid, also known as vitamin C.^[6]

Conformation

Unlike its C5 epimer iduronic acid, which may occur in a number of conformations, glucuronic acid occurs in predominantly the ⁴C₁ conformation.^[7]

Glucuronidases

Glucuronidases are those enzymes that hydrolyze the glycosidic bond between glucuronic acid and some other compound.

Notes

^ D-Glucuronic acid at Sigma-Aldrich
^ King C, Rios G, Green M, Tephly T (2000). "UDP-glucuronosyltransferases". Curr. Drug Metab. 1 (2): 143–61. doi:10.2174/1389200003339171. PMID 11465080.
^ Ohno, Shuji; Nakajin, Shizuo (2008-10-06). "Determination of mRNA Expression of Human UDP-Glucuronosyltransferases and Application for Localization in Various Human Tissues by Real-Time Reverse Transcriptase-Polymerase Chain Reaction". Drug Metabolism and Disposition (American Society for Pharmacology and Experimental Therapeutics) 37 (1): 32–40. doi:10.1124/dmd.108.023598. Retrieved 2010-11-07.
^ Bock K, Köhle C (2005). "UDP-glucuronosyltransferase 1A6: structural, functional, and regulatory aspects". Methods enzymol. 400: 57–75. doi:10.1016/S0076-6879(05)00004-2. PMID 16399343.
^ Blanc, P.J. (February 1996). "Characterization of the tea fungus metabolites". Biotechnology Letters 18 (2): 139. doi:10.1007/BF00128667. |accessdate= requires |url= (help)
^ Harvey, Richard (2011). Biochemistry (5th Edition). Philadelphia: Wolters Kluwer: Lippincott Williams and Wilkins. p. 161. ISBN 978-1-60831-412-6.
^ Ferro, D. R. Provasoli, A. (1990). "Conformer populations of L-iduronic acid residues in glycosaminoglycan sequences". Carbohydr. Res. 195 (2): 157–167. doi:10.1016/0008-6215(90)84164-P. PMID 2331699.

References

Blanc, P.J. (February 1996). "Characterization of the tea fungus metabolites". Biotechnology Letters 18 (2): 139. doi:10.1007/BF00128667. |accessdate= requires |url= (help)

Chiu SH, Huskey SW (1998). "Species differences in N-glucuronidation" (abstract). 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 human

UpToDate Contents

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English Journal

Structure characterization of a fucose-containing exopolysaccharide produced by Enterobacter cloacae Z0206.

Wang F, Yang H, Wang Y.SourceCollege of Animal Science, Zhejiang University, Key Laboratory of Animal Nutrition and Feed Science, Ministry of Agriculture (East China), Zhejiang Provincial Laboratory of Feed and Animal Nutrition, Hangzhou 310058, China.
Carbohydrate polymers.Carbohydr Polym.2013 Jan 30;92(1):503-9. doi: 10.1016/j.carbpol.2012.10.014. Epub 2012 Oct 12.
A novel high molecular weight (1.1×10(6)Da) exopolysaccharide (EPS) produced by Enterobacter cloacae Z0206 strain was isolated by column chromatography. Complete hydrolysis of the EPS followed by gas chromatography mass spectrometry (GC-MS) and high performance liquid chromatography (HPLC) analyses
PMID 23218327

Effects of glucuronic acid oligomers on the production, structure and properties of bacterial cellulose.

Ul-Islam M, Ha JH, Khan T, Park JK.SourceDepartment of Chemical Engineering, Kyungpook National University, Daegu 702-701, Republic of Korea.
Carbohydrate polymers.Carbohydr Polym.2013 Jan 30;92(1):360-6. doi: 10.1016/j.carbpol.2012.09.060. Epub 2012 Oct 2.
The addition of certain supplementary carbon sources to the culture media can influence the production, structural features and mechanical properties of bacterial cellulose (BC). In this study, different concentrations (0, 1, 2 and 4%) of a by-product, single sugar α-linked glucuronic acid-based ol
PMID 23218306

Japanese Journal

Development of Hyaluronic Acid-collagen-proteoglycan Complex (Hyaluco PG) by Hot Water Extraction from Salmon Nasal Cartilage

, , ,
Journal of Applied Glycoscience advpub(0), 2015
… Quantification of hyaluronic acid and collagen showed that the proteoglycan fraction with molecular weight ≥ 5,000,000 consisted of hyaluronic acid–collagen–proteoglycan complex. … The hot water extraction method established in this study can be used to extract the hyaluronic acid–collagen–proteoglycan complex from salmon nasal cartilage, and we have designated the salmon nasal cartilage extract obtained by this process as "Hyaluco PG". …
NAID 130005065839

Development of a new high-throughput method to determine the composition of ten monosaccharides including 4-O-methyl glucuronic acid from plant cell walls using ultra-performance liquid chromatography

, , [他],
Plant Biotechnology 32(1), 55-63, 2015
… Complete separation of a mixture of internal standards, 2-deoxy-glucose and 3-O-methyl glucose, and ten monosaccharides, consisting of seven neutral and three acidic sugars including 4-O-methyl-D-glucuronic acid, which are frequently found in plant cell wall polysaccharides, can be obtained within 7 min using this system. …
NAID 130005061608

Development of a new high-throughput method to determine the composition of ten monosaccharides including 4-O-methyl glucuronic acid from plant cell walls using ultra-performance liquid chromatography

, , ,
Plant Biotechnology advpub(0), 2015
… Complete separation of a mixture of internal standards, 2-deoxy-glucose and 3-O-methyl glucose, and ten monosaccharides, consisting of seven neutral and three acidic sugars including 4-O-methyl-D-glucuronic acid, which are frequently found in plant cell wall polysaccharides, can be obtained within 7 min using this system. …
NAID 130004834263

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★リンクテーブル★

リンク元	「glucuronate」「sodium glucuronate」
拡張検索	「uridine diphosphate glucuronic acid」「uridine diphosphate-glucuronate／glucuronic acid」
関連記事	「glucuronic」

「glucuronate」

Glucuronic acid
	IUPAC name (2S,3S,4S,5R,6R)-3,4,5,6-Tetrahydroxyoxane-2-carboxylic acid
	Other names β-D-glucopyranuronic acid
Identifiers
CAS number	6556-12-3
PubChem	441478
ChemSpider	392615
UNII	8A5D83Q4RW
DrugBank	DB03156
KEGG	C00191
MeSH	Glucuronic+acid
ChEBI	CHEBI:28860
Jmol-3D images	Image 1
	SMILES O=C(O)[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O ;
	InChI InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1 ; Key: AEMOLEFTQBMNLQ-WAXACMCWSA-N InChI=1/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1; Key: AEMOLEFTQBMNLQ-WAXACMCWBB ;
Properties
Molecular formula	C6H10O7
Molar mass	194.14 g mol−1
Melting point	159 to 161 °C (318 to 322 °F; 432 to 434 K)
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references