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53598-01-9 | NG-HydroXy-L-arginine Monoacetate
CAS No: 53598-01-9 Catalog No: AG003T1L MDL No:MFCD00216150
Product Description
Catalog Number:
AG003T1L
Chemical Name:
NG-HydroXy-L-arginine Monoacetate
CAS Number:
53598-01-9
Molecular Formula:
C8H18N4O5
Molecular Weight:
250.2523
MDL Number:
MFCD00216150
IUPAC Name:
acetic acid;(2S)-2-amino-5-[[amino-(hydroxyamino)methylidene]amino]pentanoic acid
InChI:
InChI=1S/C6H14N4O3.C2H4O2/c7-4(5(11)12)2-1-3-9-6(8)10-13;1-2(3)4/h4,13H,1-3,7H2,(H,11,12)(H3,8,9,10);1H3,(H,3,4)/t4-;/m0./s1
InChI Key:
VYMCYRPQICLHKC-WCCKRBBISA-N
SMILES:
[O-]C(=O)C.ONC(=N)NCCC[C@@H](C(=O)O)[NH3+]
Properties
Complexity:
225
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2
Defined Atom Stereocenter Count:
1
Defined Bond Stereocenter Count:
0
Exact Mass:
250.128g/mol
Formal Charge:
0
Heavy Atom Count:
17
Hydrogen Bond Acceptor Count:
7
Hydrogen Bond Donor Count:
6
Isotope Atom Count:
0
Molecular Weight:
250.255g/mol
Monoisotopic Mass:
250.128g/mol
Rotatable Bond Count:
6
Topological Polar Surface Area:
171A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
| Title | Journal |
|---|---|
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| Electron paramagnetic resonance characterization of tetrahydrobiopterin radical formation in bacterial nitric oxide synthase compared to mammalian nitric oxide synthase. | Biophysical journal 20120703 |
| Arginase 1 contributes to diminished coronary arteriolar dilation in patients with diabetes. | American journal of physiology. Heart and circulatory physiology 20110301 |
| Competition of NO synthases and arginase in the airways hyperreactivity. | General physiology and biophysics 20110301 |
| Reduction of N(ω)-hydroxy-L-arginine by the mitochondrial amidoxime reducing component (mARC). | The Biochemical journal 20110115 |
| Comparison of wild type neuronal nitric oxide synthase and its Tyr588Phe mutant towards various L-arginine analogues. | Journal of inorganic biochemistry 20101001 |
| Species differences in expression pattern of arginase isoenzymes and differential effects of arginase inhibition on collagen synthesis in human and rat pulmonary fibroblasts. | Naunyn-Schmiedeberg's archives of pharmacology 20100401 |
| Time course of desflurane-induced preconditioning in rabbits. | Journal of cardiothoracic and vascular anesthesia 20100201 |
| Single crystal structural and absorption spectral characterizations of nitric oxide synthase complexed with N(omega)-hydroxy-L-arginine and diatomic ligands. | Biochemistry 20091103 |
| EPR and ENDOR characterization of the reactive intermediates in the generation of NO by cryoreduced oxy-nitric oxide synthase from Geobacillus stearothermophilus. | Journal of the American Chemical Society 20091014 |
| Endogenous nitric oxide synthase inhibitors in sickle cell disease: abnormal levels and correlations with pulmonary hypertension, desaturation, haemolysis, organ dysfunction and death. | British journal of haematology 20090501 |
| 4,4-Difluorinated analogues of l-arginine and N(G)-hydroxy-l-arginine as mechanistic probes for nitric oxide synthase. | Bioorganic & medicinal chemistry letters 20090315 |
| The vascular effects of different arginase inhibitors in rat isolated aorta and mesenteric arteries. | British journal of pharmacology 20090101 |
| Nitric oxide, N omega-hydroxy-L-arginine and breast cancer. | Nitric oxide : biology and chemistry 20080901 |
| Thermodynamic analysis of L-arginine and N omega-hydroxy-L-arginine binding to nitric oxide synthase. | Biochimica et biophysica acta 20080501 |
| Ageing diminishes endothelium-dependent vasodilatation and tetrahydrobiopterin content in rat skeletal muscle arterioles. | The Journal of physiology 20080215 |
| Synthetic approaches to N(delta)-methylated L-arginine, N(omega)-hydroxy-L-arginine, L-citrulline, and N(delta)-cyano-L-ornithine. | The Journal of organic chemistry 20080201 |
| Effect of NO-synthase and arginase inhibition in airway hyperreactivity. | Bratislavske lekarske listy 20080101 |
| Diabetic urethropathy compounds the effects of diabetic cystopathy. | The Journal of urology 20071101 |
| Substrate- and isoform-specific dioxygen complexes of nitric oxide synthase. | Journal of the American Chemical Society 20070530 |
| Possible involvement of enhanced arginase activity due to up-regulated arginases and decreased hydroxyarginine in accelerating intimal hyperplasia with hyperglycemia. | Vascular pharmacology 20070101 |
| Reduction of Nomega-hydroxy-L-arginine to L-arginine by pig liver microsomes, mitochondria, and human liver microsomes. | Biochemical and biophysical research communications 20061020 |
| Mitochondrial arginase II modulates nitric-oxide synthesis through nonfreely exchangeable L-arginine pools in human endothelial cells. | The Journal of pharmacology and experimental therapeutics 20060901 |
| Inducible and neuronal nitric oxide synthases (NOS) have complementary roles in recovery sleep induction. | The European journal of neuroscience 20060901 |
| Discriminating formation of HNO from other reactive nitrogen oxide species. | Free radical biology & medicine 20060315 |
| Nitrosyl-heme structures of Bacillus subtilis nitric oxide synthase have implications for understanding substrate oxidation. | Biochemistry 20060227 |
| Capillary electrophoresis of the electrochemical oxidation products of Ng-hydroxy-l-arginine at physiological pH. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050925 |
| Nomega-hydroxy-L-arginine homologues and hydroxylamine as nitric oxide-dependent vasorelaxant agents. | European journal of pharmacology 20050615 |
| Role of the adventitia in the cyclic GMP-mediated relaxant effect of N-hydroxy-L-arginine in rat aorta. | Journal of vascular research 20050101 |
| Regulation of plant arginase by wounding, jasmonate, and the phytotoxin coronatine. | The Journal of biological chemistry 20041029 |
| Quantum chemical calculations of the NHA bound nitric oxide synthase active site: O2 binding and implications for the catalytic mechanism. | Journal of the American Chemical Society 20040825 |
| Nitration of a peptide phytotoxin by bacterial nitric oxide synthase. | Nature 20040506 |
| Distribution and properties of arginase in the salivary glands of four species of laboratory mammals. | Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology 20040401 |
| Modulation of intrinsic cavernous tone and nitric oxide production by arginase in rabbit corpus cavernosum. | The Journal of urology 20040101 |
| Expression of nitric oxide synthase and effect of substrate manipulation of the nitric oxide pathway in mouse ovarian follicles. | Human reproduction (Oxford, England) 20040101 |
| Arginase induction promotes Trypanosoma cruzi intracellular replication in Cruzipain-treated J774 cells through the activation of multiple signaling pathways. | European journal of immunology 20040101 |
| A tetrahydrobiopterin radical forms and then becomes reduced during Nomega-hydroxyarginine oxidation by nitric-oxide synthase. | The Journal of biological chemistry 20031121 |
| Ability of tetrahydrobiopterin analogues to support catalysis by inducible nitric oxide synthase: formation of a pterin radical is required for enzyme activity. | Biochemistry 20031118 |
| Translational control of inducible nitric oxide synthase by IL-13 and arginine availability in inflammatory macrophages. | Journal of immunology (Baltimore, Md. : 1950) 20031101 |
| Cyanide binding study of neuronal nitric oxide synthase: effects of inhibitors and mutations at the substrate binding site. | Journal of inorganic biochemistry 20030501 |
| Microperoxidase 8 catalysed nitrogen oxides formation from oxidation of N-hydroxyguanidines by hydrogen peroxide. | European journal of biochemistry 20030101 |
| Implication of intercellular adhesion molecule-1 (ICAM-1) and serum N(G)-hydroxy-L-arginine (L-NHA) in the pathogenesis of systemic sclerosis. | The Egyptian journal of immunology 20030101 |
| Involvement of NO in the endothelium-independent relaxing effects of N(omega)-hydroxy-L-arginine and other compounds bearing a C=NOH function in the rat aorta. | The Journal of pharmacology and experimental therapeutics 20021101 |
| Caspase-8-mediated BID cleavage and release of mitochondrial cytochrome c during Nomega-hydroxy-L-arginine-induced apoptosis in MDA-MB-468 cells. Antagonistic effects of L-ornithine. | The Journal of biological chemistry 20021004 |
| EPR and ENDOR characterization of intermediates in the cryoreduced oxy-nitric oxide synthase heme domain with bound L-arginine or N(G)-hydroxyarginine. | Biochemistry 20020820 |
| Glycated collagen I induces premature senescence-like phenotypic changes in endothelial cells. | Circulation research 20020628 |
| Arginase I induction in macrophages, triggered by Th2-type cytokines, supports the growth of intracellular Leishmania parasites. | Parasite immunology 20020301 |
| Effects of arginase isoforms on NO Production by nNOS. | Nitric oxide : biology and chemistry 20020201 |
| Activation of caspase-3 activity and apoptosis in MDA-MB-468 cells by N(omega)-hydroxy-L-arginine, an inhibitor of arginase, is not solely dependent on reduction in intracellular polyamines. | Carcinogenesis 20011101 |
| L-Arginine is not the limiting factor for nitric oxide synthesis by human alveolar macrophages in vitro. | The European respiratory journal 20011001 |
| Oxidation of N(omega)-hydroxyarginine analogues by NO-synthase: the simple, non amino acid N-butyl N'-hydroxyguanidine is almost as efficient an NO precursor as N(omega)-hydroxyarginine. | Journal of medicinal chemistry 20010927 |
| Classical and slow-binding inhibitors of human type II arginase. | Biochemistry 20010807 |
| X-ray absorption spectroscopic analysis of the high-spin ferriheme site in substrate-bound neuronal nitric-oxide synthase. | Journal of biochemistry 20010801 |
| Th1/Th2-regulated arginase availability modulates Leishmania infection. | Trends in parasitology 20010601 |
| Mechanism of nitric oxide synthase. Evidence that direct hydrogen atom abstraction from the O-H bond of NG-hydroxyarginine is not relevant to the mechanism. | Journal of the American Chemical Society 20010321 |
| Mechanistic and metabolic inferences from the binding of substrate analogues and products to arginase. | Biochemistry 20010306 |
| Oxidations of N(omega)-hydroxyarginine analogues and various N-hydroxyguanidines by NO synthase II: key role of tetrahydrobiopterin in the reaction mechanism and substrate selectivity. | Chemical research in toxicology 20010201 |
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