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5262-39-5,MFCD00913253
Catalog No.:AA00I9C9

5262-39-5 | N-Oxalylglycine

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5mg
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in stock  
$26.00   $18.00
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10mg
95%
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$39.00   $27.00
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100mg
98%
in stock  
$45.00   $32.00
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250mg
98%
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$55.00   $39.00
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1g
98%
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$151.00   $106.00
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5g
98%
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$394.00   $276.00
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25g
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$1,905.00   $1,334.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00I9C9
Chemical Name:
N-Oxalylglycine
CAS Number:
5262-39-5
Molecular Formula:
C4H5NO5
Molecular Weight:
147.0862
MDL Number:
MFCD00913253
SMILES:
OC(=O)CNC(=O)C(=O)O
Properties
Properties
 
Form:
Solid  
Solubility:
deionized water: >10mg/mL  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
175  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
3  
XLogP3:
-0.9  

Downstream Synthesis Route

[1]Oparin[BiochemischeZeitschrift,1921,vol.124,p.92][Izv.ross.Akad.,vol.<6>16,p.543][ChemischesZentralblatt,1925,vol.96,#II,p.728]

[2]Oparin[BiochemischeZeitschrift,1921,vol.124,p.92][Izv.ross.Akad.,vol.<6>16,p.543][ChemischesZentralblatt,1925,vol.96,#II,p.728]

[1]Pollack[1906,vol.7,p.18]

[2]Viscontini[HelveticaChimicaActa,1946,vol.29,p.1496]

[1]Viscontini[HelveticaChimicaActa,1946,vol.29,p.1496]

N-oxamoyl-glycine 
  5262-39-5 

[1]Kerp;Unger[ChemischeBerichte,1897,vol.30,p.590]

[1]Kerp;Unger[ChemischeBerichte,1897,vol.30,p.590]Kraemer[ChemischeBerichte,1906,vol.39,p.4386]

Literature

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Journal: Chemico-biological interactions 20160125

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Title: Selective stabilization of HIF-1α in renal tubular cells by 2-oxoglutarate analogues.

Journal: The American journal of pathology 20121101

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Journal: Journal of endodontics 20121101

Title: α-Ketoglutarate-related inhibitors of HIF prolyl hydroxylases are substrates of renal organic anion transporters 1 (OAT1) and 4 (OAT4).

Journal: Pflugers Archiv : European journal of physiology 20121001

Title: Activation of the prolyl-hydroxylase oxygen-sensing signal cascade leads to AMPK activation in cardiomyocytes.

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Title: Increased activation of the hypoxia-inducible factor pathway in varicose veins.

Journal: Journal of vascular surgery 20120501

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Journal: Journal of medicinal chemistry 20120412

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Journal: Journal of medicinal chemistry 20120308

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Journal: Journal of hepatology 20120201

Title: Inhibition of prolyl hydroxylases by dimethyloxaloylglycine after stroke reduces ischemic brain injury and requires hypoxia inducible factor-1α.

Journal: Neurobiology of disease 20120201

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Journal: Journal of dermatological science 20120201

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Title: Activation of hypoxia-inducible factor-1 ameliorates postischemic renal injury via inducible nitric oxide synthase.

Journal: Molecular and cellular biochemistry 20111201

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Title: Activation of hypoxia-inducible factor-1 protects airway epithelium against oxidant-induced barrier dysfunction.

Journal: American journal of physiology. Lung cellular and molecular physiology 20111201

Title: Hypoxia induced expression of histone lysine demethylases: implications in oxygen-dependent retinal neovascular diseases.

Journal: Biochemical and biophysical research communications 20111118

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Journal: American journal of respiratory cell and molecular biology 20111101

Title: Curcumin provides potential protection against the activation of hypoxia and prolyl 4-hydroxylase inhibitors on prostate-specific antigen expression in human prostate carcinoma cells.

Journal: Molecular nutrition & food research 20111101

Title: Longitudinal quantification of inflammation in the murine dextran sodium sulfate-induced colitis model using μPET/CT.

Journal: Inflammatory bowel diseases 20111001

Title: Inhibition of prolyl hydroxylase domain-containing protein downregulates vascular angiotensin II type 1 receptor.

Journal: Hypertension (Dallas, Tex. : 1979) 20110901

Title: The hydroxylase inhibitor dimethyloxallyl glycine attenuates endotoxic shock via alternative activation of macrophages and IL-10 production by B1 cells.

Journal: Shock (Augusta, Ga.) 20110901

Title: Dimethyloxalylglycine stabilizes HIF-1α in cultured human endothelial cells and increases random-pattern skin flap survival in vivo.

Journal: Plastic and reconstructive surgery 20110801

Title: Systemic pretreatment with dimethyloxalylglycine increases myocardial HIF-1α and VEGF production and improves functional recovery after acute ischemia/reperfusion.

Journal: Surgery 20110801

Title: Apigenin down-regulates the hypoxia response genes: HIF-1α, GLUT-1, and VEGF in human pancreatic cancer cells.

Journal: The Journal of surgical research 20110515

Title: Metabolic reprogramming by HIF-1 promotes the survival of bone marrow-derived angiogenic cells in ischemic tissue.

Journal: Blood 20110505

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Journal: Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition 20110501

Title: Hypoxia-inducible factor-1α-dependent protection from intestinal ischemia/reperfusion injury involves ecto-5'-nucleotidase (CD73) and the A2B adenosine receptor.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20110401

Title: Factor inhibiting HIF (FIH-1) promotes renal cancer cell survival by protecting cells from HIF-1α-mediated apoptosis.

Journal: British journal of cancer 20110329

Title: HIF1alpha synergizes with glucocorticoids to promote BFU-E progenitor self-renewal.

Journal: Blood 20110324

Title: Structural basis for human PHF2 Jumonji domain interaction with metal ions.

Journal: Journal of molecular biology 20110211

Title: Hydroxylase inhibition attenuates colonic epithelial secretory function and ameliorates experimental diarrhea.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20110201

Title: Neuroprotection by dimethyloxalylglycine following permanent and transient focal cerebral ischemia in rats.

Journal: Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20110101

Title: Rhapontigenin inhibited hypoxia inducible factor 1 alpha accumulation and angiogenesis in hypoxic PC-3 prostate cancer cells.

Journal: Biological & pharmaceutical bulletin 20110101

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Journal: Current chemical genomics 20110101

Title: Methods for Activity Analysis of the Proteins that Regulate Histone Methylation.

Journal: Current chemical genomics 20110101

Title: Activation of Hif1α by the prolylhydroxylase inhibitor dimethyoxalyglycine decreases radiosensitivity.

Journal: PloS one 20110101

Title: von Hippel-Lindau β-domain-luciferase fusion protein as a bioluminescent hydroxyproline sensor for a hypoxia-inducible factor prolyl hydroxylase assay.

Journal: Analytical biochemistry 20101215

Title: Renal protection in chronic kidney disease: hypoxia-inducible factor activation vs. angiotensin II blockade.

Journal: American journal of physiology. Renal physiology 20101201

Title: Hydroxylase inhibition abrogates TNF-alpha-induced intestinal epithelial damage by hypoxia-inducible factor-1-dependent repression of FADD.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20101115

Title: Structural basis for binding of cyclic 2-oxoglutarate analogues to factor-inhibiting hypoxia-inducible factor.

Journal: Bioorganic & medicinal chemistry letters 20101015

Title: Hypoxia and preeclampsia: increased expression of urocortin 2 and urocortin 3.

Journal: Reproductive sciences (Thousand Oaks, Calif.) 20100901

Title: Force field design and molecular dynamics simulations of factor-inhibiting HIF-1 and its complex with known inhibitors: implications for rational inhibitor design.

Journal: Journal of molecular graphics & modelling 20100901

Title: Design, synthesis, enzyme-inhibitory activity, and effect on human cancer cells of a novel series of jumonji domain-containing protein 2 histone demethylase inhibitors.

Journal: Journal of medicinal chemistry 20100812

Title: Acute hypoxia induces HIF-independent monocyte adhesion to endothelial cells through increased intercellular adhesion molecule-1 expression: the role of hypoxic inhibition of prolyl hydroxylase activity for the induction of NF-kappa B.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20100801

Title: Hydroxylase inhibition reduces synaptic transmission and protects against a glutamate-induced ischemia in the CA1 region of the rat hippocampus.

Journal: Neuroscience 20100602

Title: Regulation of the matricellular proteins CYR61 (CCN1) and NOV (CCN3) by hypoxia-inducible factor-1{alpha} and transforming-growth factor-{beta}3 in the human trophoblast.

Journal: Endocrinology 20100601

Title: Prolyl hydroxylase EGLN3 regulates skeletal myoblast differentiation through an NF-kappaB-dependent pathway.

Journal: The Journal of biological chemistry 20100319

Title: Characterization of connective tissue growth factor expression in primary cultures of human tubular epithelial cells: modulation by hypoxia.

Journal: American journal of physiology. Renal physiology 20100301

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Journal: Cancer science 20100101

Title: Quantitative high-throughput screening identifies 8-hydroxyquinolines as cell-active histone demethylase inhibitors.

Journal: PloS one 20100101

Title: Inhibition of prolyl hydroxylase domain-containing protein suppressed lipopolysaccharide-induced TNF-alpha expression.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20091201

Title: Combined analysis of hypoxia-inducible factor 1 alpha and metallothionein indicates an aggressive subtype of colorectal carcinoma.

Journal: International journal of colorectal disease 20091101

Title: Hypoxia interferes with connective tissue growth factor (CTGF) gene expression in human proximal tubular cell lines.

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Title: Prolyl hydroxylase inhibitors increase neoangiogenesis and callus formation following femur fracture in mice.

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Title: Adenosine A2A receptor is a unique angiogenic target of HIF-2alpha in pulmonary endothelial cells.

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Title: Application of a proteolysis/mass spectrometry method for investigating the effects of inhibitors on hydroxylase structure.

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Title: Prolyl hydroxylase inhibitor dimethyloxalylglycine enhances mesenchymal stem cell survival.

Journal: Journal of cellular biochemistry 20090401

Title: Proteomics-based identification of novel factor inhibiting hypoxia-inducible factor (FIH) substrates indicates widespread asparaginyl hydroxylation of ankyrin repeat domain-containing proteins.

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Title: Hypoxia-inducible factor-1 is central to cardioprotection: a new paradigm for ischemic preconditioning.

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Title: DHEA decreases HIF-1alpha accumulation under hypoxia in human pulmonary artery cells: potential role in the treatment of pulmonary arterial hypertension.

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Title: The hydroxylase inhibitor dimethyloxalylglycine is protective in a murine model of colitis.

Journal: Gastroenterology 20080101

Title: Role of hypoxia-inducible factor 1 alpha in the integrity of articular cartilage in murine knee joints.

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Title: Prolyl hydroxylase inhibitors delay neuronal cell death caused by trophic factor deprivation.

Journal: Journal of neurochemistry 20071201

Title: HIF-1 regulates hypoxia- and insulin-induced expression of apelin in adipocytes.

Journal: American journal of physiology. Endocrinology and metabolism 20071201

Title: Hypoxia-inducible factor 1alpha is involved in the prostaglandin metabolism of osteoarthritic cartilage through up-regulation of microsomal prostaglandin E synthase 1 in articular chondrocytes.

Journal: Arthritis and rheumatism 20071201

Title: Hypoxia stimulates degradation of 3-hydroxy-3-methylglutaryl-coenzyme A reductase through accumulation of lanosterol and hypoxia-inducible factor-mediated induction of insigs.

Journal: The Journal of biological chemistry 20070914

Title: Effect of chemical stabilizers of hypoxia-inducible factors on early lung development.

Journal: American journal of physiology. Lung cellular and molecular physiology 20070901

Title: HIF stabilizing agents: shotgun or scalpel?

Journal: American journal of physiology. Lung cellular and molecular physiology 20070901

Title: Prolyl hydroxylase inhibitor treatment confers whole-animal hypoxia tolerance.

Journal: Acta physiologica (Oxford, England) 20070601

Title: Purification and characterization of the FeII- and alpha-ketoglutarate-dependent xanthine hydroxylase from Aspergillus nidulans.

Journal: Biochemistry 20070508

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Journal: Microvascular research 20070501

Title: Toxic effects of cobalt in primary cultures of mouse astrocytes. Similarities with hypoxia and role of HIF-1alpha.

Journal: Biochemical pharmacology 20070301

Title: The prolyl hydroxylase oxygen-sensing pathway is cytoprotective and allows maintenance of mitochondrial membrane potential during metabolic inhibition.

Journal: American journal of physiology. Cell physiology 20070201

Title: Induction of activating transcription factor 3 by anoxia is independent of p53 and the hypoxic HIF signalling pathway.

Journal: Oncogene 20070111

Title: Expression of HIF prolyl hydroxylase isozymes in growth plate chondrocytes: relationship between maturation and apoptotic sensitivity.

Journal: Journal of cellular physiology 20070101

Title: Concordant regulation of gene expression by hypoxia and 2-oxoglutarate-dependent dioxygenase inhibition: the role of HIF-1alpha, HIF-2alpha, and other pathways.

Journal: The Journal of biological chemistry 20060602

Title: Hypoxia dysregulates the production of adiponectin and plasminogen activator inhibitor-1 independent of reactive oxygen species in adipocytes.

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Title: Kinetic and spectroscopic investigation of CoII, NiII, and N-oxalylglycine inhibition of the FeII/alpha-ketoglutarate dioxygenase, TauD.

Journal: Biochemical and biophysical research communications 20051209

Title: HIF-1 activation attenuates postischemic myocardial injury: role for heme oxygenase-1 in modulating microvascular chemokine generation.

Journal: American journal of physiology. Heart and circulatory physiology 20050801

Title: Activation of hypoxia-induced transcription in normoxia.

Journal: Experimental cell research 20050515

Title: Nitric oxide reverses desferrioxamine- and hypoxia-evoked HIF-1alpha accumulation--implications for prolyl hydroxylase activity and iron.

Journal: Experimental cell research 20050515

Title: Oligomycin inhibits HIF-1alpha expression in hypoxic tumor cells.

Journal: American journal of physiology. Cell physiology 20050501

Title: Expression and hypoxia-responsiveness of 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 4 in mammary gland malignant cell lines.

Journal: Acta biochimica Polonica 20050101

Title: Inhibition of endogenous HIF inactivation induces angiogenesis in ischaemic skeletal muscles of mice.

Journal: The Journal of physiology 20041001

Title: Role of prolyl hydroxylation in oncogenically stabilized hypoxia-inducible factor-1alpha.

Journal: The Journal of biological chemistry 20021018

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Tags:5262-39-5 Molecular Formula|5262-39-5 MDL|5262-39-5 SMILES|5262-39-5 N-Oxalylglycine