オキサロコハク酸
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)』「2015/09/20 01:37:13」(JST)
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Oxalosuccinic acid
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Names |
IUPAC name
1-Oxopropane-1,2,3-tricarboxylic acid
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Identifiers |
CAS Registry Number
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1948-82-9 Y |
ChEBI |
CHEBI:7815 N |
ChemSpider |
947 N |
InChI
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InChI=1S/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13) N
Key: UFSCUAXLTRFIDC-UHFFFAOYSA-N N
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InChI=1/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13)
Key: UFSCUAXLTRFIDC-UHFFFAOYAK
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Jmol-3D images |
Image |
KEGG |
C05379 N |
PubChem |
972 |
SMILES
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C(C(C(=O)C(=O)O)C(=O)O)C(=O)O
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Properties |
Chemical formula
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C6H6O7 |
Molar mass |
190.108 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is: Y/N?) |
Infobox references |
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Oxalosuccinic acid is a substrate of the citric acid cycle. It is acted upon by isocitrate dehydrogenase. Salts and esters of oxalosuccinic acid are known as oxalosuccinates.
Oxalosuccinic acid/oxalosuccinate is an unstable 6-carbon intermediate in the tricarboxylic acid cycle. It's an alpha-keto compound, formed during the oxidative decarboxylation of isocitrate to alpha-ketoglutarate, which is catalyzed by the enzyme isocitrate dehydrogenase. Oxalosuccinate never leaves the active site of the enzyme, however it's unstable and immediately undergoes decarboxylation to produce the 5-carbon compound, alpha-ketoglutarate.
Citric acid cycle metabolic pathway |
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Oxaloacetate |
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Malate |
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Fumarate |
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Succinate |
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Succinyl-CoA |
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Acetyl-CoA |
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NADH + H+ |
NAD+ |
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H2O |
FADH2 |
FAD |
CoA + ATP(GTP) |
Pi + ADP(GDP) |
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+ |
H2O |
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NADH + H+ + CO2 |
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CoA |
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NAD+ |
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H2O |
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H2O |
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NAD(P)+ |
NAD(P)H + H+ |
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CO2 |
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Citrate |
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cis-Aconitate |
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Isocitrate |
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Oxalosuccinate |
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α-Ketoglutarate |
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Index of inborn errors of metabolism
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Description |
- Metabolism
- Enzymes and pathways: citric acid cycle
- pentose phosphate
- glycoproteins
- glycosaminoglycans
- phospholipid
- cholesterol and steroid
- sphingolipids
- eicosanoids
- amino acid
- urea cycle
- nucleotide
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Disorders |
- Citric acid cycle and electron transport chain
- Glycoprotein
- Proteoglycan
- Fatty-acid
- Phospholipid
- Cholesterol and steroid
- Eicosanoid
- Amino acid
- Purine-pyrimidine
- Heme metabolism
- Symptoms and signs
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Treatment |
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UpToDate Contents
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English Journal
- Oxalomalate affects the inducible nitric oxide synthase expression and activity.
- Irace C1, Esposito G, Maffettone C, Rossi A, Festa M, Iuvone T, Santamaria R, Sautebin L, Carnuccio R, Colonna A.Author information 1Dipartimento di Farmacologia Sperimentale, Università di Napoli Federico II, via D. Montesano 49, 80131-Napoli, Italy.AbstractInducible nitric oxide synthase (iNOS) is an homodimeric enzyme which produces large amounts of nitric oxide (NO) in response to inflammatory stimuli. Several factors affect the synthesis and catalytic activity of iNOS. Particularly, dimerization of NOS monomers is promoted by heme, whereas an intracellular depletion of heme and/or L-arginine considerably decreases NOS resistance to proteolysis. In this study, we found that oxalomalate (OMA, oxalomalic acid, alpha-hydroxy-beta-oxalosuccinic acid), an inhibitor of both aconitase and NADP-dependent isocitrate dehydrogenase, inhibited nitrite production and iNOS protein expression in lipopolysaccharide (LPS)-activated J774 macrophages, without affecting iNOS mRNA content. Furthermore, injection of OMA precursors to LPS-stimulated rats also decreased nitrite production and iNOS expression in isolated peritoneal macrophages. Interestingly, alpha-ketoglutarate or succinyl-CoA administration reversed OMA effect on NO production, thus correlating NO biosynthesis with the anabolic capacity of Krebs cycle. When protein synthesis was blocked by cycloheximide in LPS-activated J774 cells treated with OMA, iNOS protein levels, evaluated by Western blot analysis and (35)S-metabolic labelling, were decreased, suggesting that OMA reduces iNOS biosynthesis and induces an increase in the degradation rate of iNOS protein. Moreover, we showed that OMA inhibits the activity of the iNOS from lung of LPS-treated rats by enzymatic assay. Our results, demonstrating that OMA acts regulating synthesis, catalytic activity and degradation of iNOS, suggest that this compound might have a potential role in reducing the NO overproduction occurring in some pathological conditions.
- Life sciences.Life Sci.2007 Mar 13;80(14):1282-91. Epub 2006 Dec 22.
- Inducible nitric oxide synthase (iNOS) is an homodimeric enzyme which produces large amounts of nitric oxide (NO) in response to inflammatory stimuli. Several factors affect the synthesis and catalytic activity of iNOS. Particularly, dimerization of NOS monomers is promoted by heme, whereas an intra
- PMID 17257628
- Induction of ferritin expression by oxalomalate.
- Santamaria R1, Irace C, Festa M, Maffettone C, Colonna A.Author information 1Dipartimento di Farmacologia Sperimentale, Università di Napoli Federico II, Via D. Montesano 49, 80131 Naples, Italy.AbstractFerritin is a ubiquitous protein required for intracellular iron storage; its biosynthesis is mainly regulated by iron-regulatory proteins (IRP1 and IRP2) at post-transcriptional level. This regulation prevents iron excess from promoting the formation of reactive oxygen species (ROS). IRP1 is regulated by such factors as intracellular iron levels, the oxidants H(2)O(2) and NO. We recently demonstrated that oxalomalate (OMA, alpha-hydroxy-beta-oxalosuccinic acid), a competitive inhibitor of aconitase, which is an enzyme of the citric acid cycle, remarkably decreases the binding activity of IRP1. The aim of the present study was to investigate whether this molecule could affect the expression of ferritin. The RNA-binding activity of IRP1, evaluated by gel retardation assay, decreased after treatment of several cell lines with 5 mM OMA, with a maximal decrease of about 3-fold after 6 h. This effect remained almost constant up to 48 h after which it returned to basal levels. Intracellular ferritin levels, determined by Western blot analysis, increased in correlation with the OMA-induced decrease of IRP1 binding activity. Furthermore, treatment of cells with OMA caused a rise in ferritin mRNA levels. Interestingly, in cells exposed to iron challenge, OMA-induced overexpression of ferritin prevented formation of ROS and cellular lipid peroxidation. These data show that an inhibitor of aconitase, OMA, besides being involved in energetic metabolism, is able to control ferritin expression, probably through molecular mechanisms of either post-transcriptional regulation or transcriptional modulation, with advantageous consequences for the cell.
- Biochimica et biophysica acta.Biochim Biophys Acta.2004 May 3;1691(2-3):151-9.
- Ferritin is a ubiquitous protein required for intracellular iron storage; its biosynthesis is mainly regulated by iron-regulatory proteins (IRP1 and IRP2) at post-transcriptional level. This regulation prevents iron excess from promoting the formation of reactive oxygen species (ROS). IRP1 is regula
- PMID 15110995
- Oxalomalate, a competitive inhibitor of aconitase, modulates the RNA-binding activity of iron-regulatory proteins.
- Festa M1, Colonna A, Pietropaolo C, Ruffo A.Author information 1Dipartimento di Farmacologia Sperimentale, Università di Napoli 'Federico II', Via Domenico Montesano 49, I-80131 Napoli, Italy.AbstractWe investigated the effect of oxalomalate (OMA, alpha-hydroxy-beta-oxalosuccinic acid), a competitive inhibitor of aconitase, on the RNA-binding activity of the iron-regulatory proteins (IRP1 and IRP2) that control the post-transcriptional expression of various proteins involved in iron metabolism. The RNA-binding activity of IRP was evaluated by electrophoretic mobility-shift assay of cell lysates from 3T3-L1 mouse fibroblasts, SH-SY5Y human cells and mouse livers incubated in vitro with OMA, with and without 2-mercaptoethanol (2-ME). Analogous experiments were performed in vivo by prolonged incubation (72 h) of 3T3-L1 cells with OMA, and by injecting young mice with equimolar concentrations of oxaloacetate and glyoxylate, which are the precursors of OMA synthesis. OMA remarkably decreased the binding activity of IRP1 and, when present, of IRP2, in all samples analysed. In addition, the recovery of IRP1 by 2-ME in the presence of OMA was constantly lower versus control values. These findings suggest that the severe decrease in IRP1 RNA-binding activity depends on: (i) linking of OMA to the active site of aconitase, which prevents the switch to IRP1 and explains resistance to the reducing agents, and (ii) possible interaction of OMA with some functional amino acid residues in IRP that are responsible for binding to the specific mRNA sequences involved in the regulation of iron metabolism.
- The Biochemical journal.Biochem J.2000 Jun 1;348 Pt 2:315-20.
- We investigated the effect of oxalomalate (OMA, alpha-hydroxy-beta-oxalosuccinic acid), a competitive inhibitor of aconitase, on the RNA-binding activity of the iron-regulatory proteins (IRP1 and IRP2) that control the post-transcriptional expression of various proteins involved in iron metabolism.
- PMID 10816424
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- ox·a·lo·suc·cin·ic ac·id / ˈɒk sə loʊ səkˈsɪn ɪk, ˌɒk-, ɒkˈsæl oʊ-, -ˌsæl-/ Show Spelled [ok-s uh-loh-s uh k-sin-ik, ok-, ok-sal-oh-, -sal-] Show IPA noun Biochemistry. an organic acid, C 6 H 6 O 7, that is an intermediate formed by the ...
- Added to Favorites Dictionary Thesaurus Word Dynamo Quotes Reference Translator Spanish Log In Sign Up Premium Introducing a cool new way to learn! oxalosuccinic-acid ox·a·lo·suc·cin·ic ac·id / ˈɒk sə loʊ səkˈsɪn ɪk, ˌɒk ...
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