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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"

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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

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/03/27 16:11:37」(JST)

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L-Iduronic acid (IdoA) is the major uronic acid component of the glycosaminoglycans (GAGs) dermatan sulfate, and heparin. It is also present in heparan sulfate although here in a minor amount relative to its carbon-5 epimer glucuronic acid.

IdoA is a hexapyranose sugar. Most hexapyranoses are stable in one of two chair conformations ¹C₄ or ⁴C₁. L-iduronate is different and adopts more than one solution conformation, with an equilibrium existing between three low-energy conformers. These are the ¹C₄ and ⁴C₁ chair forms and an additional ²S₀ skew-boat conformation.

IdoA may be modified by the addition of an O-sulfate group at carbon position 2 to form 2-O-sulfo-L-iduronic acid (IdoA2S).

In 2000, LK Hallak described the importance of this sugar in respiratory syncytial virus infection. Dermatan sulfate and heparan sulfate were the only GAGs containing IdoA, and they were the only ones that inhibited RSV infection in cell culture.^[1]

When internally positioned within an oligosaccharide, the ¹C₄ and ²S₀ conformations (shown below for IdoA2S) predominate.

Proton NMR spectroscopy can be used to track changes in the balance of this equilibrium.^[2]

IdoA(2S)¹C₄ conformation
IdoA(2S)²S₀ conformation

References

^ Hallak LK, Collins PL, Knudson W, Peeples ME (2000). "Iduronic acid-containing glycosaminoglycans on target cells are required for efficient respiratory syncytial virus infection". Virology 271 (2): 264–75. doi:10.1006/viro.2000.0293. PMID 10860881.
^ 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.

UpToDate Contents

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1. 尿酸のバランス uric acid balance
2. 出産時の臍帯血酸塩基分析 umbilical cord blood acid base analysis at delivery
3. 妊娠中の葉酸補充 folic acid supplementation in pregnancy
4. ポルフィリン症：概要 porphyrias an overview
5. 疾患予防におけるビタミン補給 vitamin supplementation in disease prevention

English Journal

Controllable production of low molecular weight heparins by combinations of heparinase I/II/III.

Wu J, Zhang C, Mei X, Li Y, Xing XH.SourceKey Laboratory for Industrial Biocatalysis of Ministry of Education, Institute of Biochemical Engineering, Department of Chemical Engineering, Tsinghua University, Haidian, Beijing 100084, People's Republic of China. Electronic address: wujingjun2009@foxmail.com.
Carbohydrate polymers.Carbohydr Polym.2014 Jan 30;101:484-92. doi: 10.1016/j.carbpol.2013.09.052. Epub 2013 Sep 23.
Enzymatic depolymerization of heparin by heparinases is promising for production of low molecular weight heparins (LMWHs) as anticoagulants, due to its mild reaction conditions and high selectivity. Here, different heparinase combinations were used to depolymerize heparin. Heparinase I and heparinas
PMID 24299802

Analysis of Drosophila Glucuronyl C5-Epimerase: IMPLICATIONS FOR DEVELOPMENTAL ROLES OF HEPARAN SULFATE SULFATION COMPENSATION AND 2-O-SULFATED GLUCURONIC ACID.

Dejima K, Takemura M, Nakato E, Peterson J, Hayashi Y, Kinoshita-Toyoda A, Toyoda H, Nakato H.SourceFrom the Department of Genetics, Cell Biology, and Development, University of Minnesota, Minneapolis, Minnesota 55455 and.
The Journal of biological chemistry.J Biol Chem.2013 Nov 29;288(48):34384-93. doi: 10.1074/jbc.M113.499269. Epub 2013 Oct 16.
During the biosynthesis of heparan sulfate (HS), glucuronyl C5-epimerase (Hsepi) catalyzes C5-epimerization of glucuronic acid (GlcA), converting it to iduronic acid (IdoA). Because HS 2-O-sulfotransferase (Hs2st) shows a strong substrate preference for IdoA over GlcA, C5-epimerization is required f
PMID 24133213

Structural features of glycol-split low-molecular-weight heparins and their heparin lyase generated fragments.

Alekseeva A, Casu B, Cassinelli G, Guerrini M, Torri G, Naggi A.SourceRonzoni Institute for Chemical and Biochemical Research, Via Giuseppe Colombo 81, 20133, Milan, Italy.
Analytical and bioanalytical chemistry.Anal Bioanal Chem.2013 Nov 20. [Epub ahead of print]
Periodate oxidation followed by borohydride reduction converts the well-known antithrombotics heparin and low-molecular-weight heparins (LMWHs) into their "glycol-split" (gs) derivatives of the "reduced oxyheparin" (RO) type, some of which are currently being developed as potential anti-cancer and a
PMID 24253408

Japanese Journal

ヘパリンおよびヘパラン硫酸に関連するオリゴ糖鎖の化学合成

Zulueta Medel Manuel L,Lin Shu-Yi,Hung Shang-Cheng
Trends in glycoscience and glycotechnology 25(144-146), 141-158, 2013-07
NAID 40019983189

ヘパリンおよびヘパラン硫酸に関連するオリゴ糖鎖の化学合成

Zulueta Medel Manuel L,Lin Shu-Yi,Hung Shang-Cheng
Trends in Glycoscience and Glycotechnology 25(144), 141-158, 2013
ヘパリンおよびヘパラン硫酸（HS）は、複雑な骨格を持つ多糖であり、多くのタンパク質の活性を媒介・調節している。それらのタンパク質は、多様な硫酸化パターンで修飾された繰返し2糖骨格を持つ糖鎖と相互作用する。相互作用に関する分子レベルの詳細な知見は、新しい形態の診断薬や治療薬の開発に役立つと期待される。ヘパリンおよびHS骨格オリゴ糖の化学合成は、構造活性相関研究のための構造が明確な試料の入手を容易 …
NAID 130004841372

Expression of chondroitin-glucuronate C5-epimerase and cellular immune responses in patients with hepatocellular carcinoma

Mizukoshi Eishiro,Fushimi Kazumi,Arai Kuniaki,Yamashita Tatsuya,Honda Masao,Kaneko Shuichi
Liver International 32(10), 1516-1526, 2012-11
… Aims: Chondroitin-glucuronate C5-epimerase is an enzyme that converts D-glucuronic acid to L-iduronic acid residues in dermatan sulphate biosynthesis. …
NAID 120004997021

Related Pictures

★リンクテーブル★

リンク元	「iduronate」
拡張検索	「β-D-glucopyranosiduronic acid」
関連記事	「iduronic」

「iduronate」

L-Iduronic acid
Names
	IUPAC name L-idopyranuronic acid
	Other names L-Iduronic acid, D-ido-Hexuronic acid, IdoA
Identifiers
CAS Number	3402-98-0
ChEBI	CHEBI:28481
ChemSpider	10051462
Jmol interactive 3D	Image
KEGG	C06472
MeSH	Iduronic+acid
PubChem	11877134
	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)/p-1/t1-,2-,3+,4+,6+/m0/s1 Key: AEMOLEFTQBMNLQ-VCSGLWQLSA-M ; 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)/p-1/t1-,2-,3+,4+,6+/m0/s1 Key: AEMOLEFTQBMNLQ-QQSWGHAIBB ;
	SMILES [O-]C(=O)[C@@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O ;
Properties
Chemical formula	C6H10O7
Molar mass	194.139 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references