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157-03-9,MFCD00037218
Catalog No.:AA001P2B

157-03-9 | L-Norleucine, 6-diazo-5-oxo-

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10mg
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25mg
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50mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA001P2B
Chemical Name:
L-Norleucine, 6-diazo-5-oxo-
CAS Number:
157-03-9
Molecular Formula:
C6H9N3O3
Molecular Weight:
171.1540
MDL Number:
MFCD00037218
SMILES:
[N-]=[N+]=CC(=O)CC[C@@H](C(=O)O)N
Properties
Computed Properties
 
Complexity:
232  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
12  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
5  
Undefined Bond Stereocenter Count:
1  
XLogP3:
-3.5  

Literature

Title: Preventing Allograft Rejection by Targeting Immune Metabolism.

Journal: Cell reports 20151027

Title: Computational and experimental analysis identified 6-diazo-5-oxonorleucine as a potential agent for treating infection by Plasmodium falciparum.

Journal: Infection, genetics and evolution : journal of molecular epidemiology and evolutionary genetics in infectious diseases 20131201

Title: Mycobacterium tuberculosis prokaryotic ubiquitin-like protein-deconjugating enzyme is an unusual aspartate amidase.

Journal: The Journal of biological chemistry 20121026

Title: Glutamate released by Japanese encephalitis virus-infected microglia involves TNF-α signaling and contributes to neuronal death.

Journal: Glia 20120301

Title: Hyperglycemia and endothelial dysfunction in atherosclerosis: lessons from type 1 diabetes.

Journal: International journal of vascular medicine 20120101

Title: The hypothalamus mediates the effect of cerebellar fastigial nuclear glutamatergic neurons on humoral immunity.

Journal: Neuro endocrinology letters 20120101

Title: A simple method for measuring intracellular activities of glutamine synthetase and glutaminase in glial cells.

Journal: American journal of physiology. Cell physiology 20111001

Title: Glutamine analogs promote cytoophidium assembly in human and Drosophila cells.

Journal: Journal of genetics and genomics = Yi chuan xue bao 20110920

Title: Metabolism and brain cancer.

Journal: Clinics (Sao Paulo, Brazil) 20110601

Title: Evidence that chromium modulates cellular cholesterol homeostasis and ABCA1 functionality impaired by hyperinsulinemia--brief report.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20110501

Title: A practical method for cell-free protein synthesis to avoid stable isotope scrambling and dilution.

Journal: Analytical biochemistry 20110415

Title: Hijacking a biosynthetic pathway yields a glycosyltransferase inhibitor within cells.

Journal: Nature chemical biology 20110301

Title: Hyperammonemia increases the expression and activity of the glutamine/arginine transporter y+ LAT2 in rat cerebral cortex: implications for the nitric oxide/cGMP pathway.

Journal: Neurochemistry international 20110201

Title: Synergistic action of hypoosmolarity and glutamine in inducing acute swelling of retinal glial (Müller) cells.

Journal: Glia 20110201

Title: Increased expression of cystine/glutamate antiporter in multiple sclerosis.

Journal: Journal of neuroinflammation 20110101

Title: Predicting selective drug targets in cancer through metabolic networks.

Journal: Molecular systems biology 20110101

Title: Oncogenic stress induced by acute hyper-activation of Bcr-Abl leads to cell death upon induction of excessive aerobic glycolysis.

Journal: PloS one 20110101

Title: Induction of cytoplasmic rods and rings structures by inhibition of the CTP and GTP synthetic pathway in mammalian cells.

Journal: PloS one 20110101

Title: Glutamine targeting inhibits systemic metastasis in the VM-M3 murine tumor model.

Journal: International journal of cancer 20101115

Title: Partial purification and characterization of glutaminase from Lactobacillus reuteri KCTC3594.

Journal: Applied biochemistry and biotechnology 20100901

Title: The metabolic enzyme CTP synthase forms cytoskeletal filaments.

Journal: Nature cell biology 20100801

Title: O-GlcNAc Modification: Friend or Foe in Diabetic Cardiovascular Disease.

Journal: Korean diabetes journal 20100801

Title: Characteristic increase in nucleocytoplasmic protein glycosylation by O-GlcNAc in 3T3-L1 adipocyte differentiation.

Journal: Biochemical and biophysical research communications 20100730

Title: Peripheral inhibition of glutaminase reduces carrageenan-induced Fos expression in the superficial dorsal horn of the rat.

Journal: Neuroscience letters 20100326

Title: Hexosamine biosynthesis pathway flux promotes endoplasmic reticulum stress, lipid accumulation, and inflammatory gene expression in hepatic cells.

Journal: American journal of physiology. Endocrinology and metabolism 20100301

Title: Influence of glucosamine on glomerular mesangial cell turnover: implications for hyperglycemia and hexosamine pathway flux.

Journal: American journal of physiology. Endocrinology and metabolism 20100201

Title: Peritoneal adhesion and angiogenesis in ovarian carcinoma are inversely regulated by hyaluronan: the role of gonadotropins.

Journal: Neoplasia (New York, N.Y.) 20100101

Title: Cancer as a metabolic disease.

Journal: Nutrition & metabolism 20100101

Title: Cell-cycle inhibition by Helicobacter pylori L-asparaginase.

Journal: PloS one 20100101

Title: O-glycosylation regulates ubiquitination and degradation of the anti-inflammatory protein A20 to accelerate atherosclerosis in diabetic ApoE-null mice.

Journal: PloS one 20100101

Title: High glucose induces transactivation of the alpha2-HS glycoprotein gene through the ERK1/2 signaling pathway.

Journal: Journal of atherosclerosis and thrombosis 20090801

Title: Glutamine inhibits ammonia-induced accumulation of cGMP in rat striatum limiting arginine supply for NO synthesis.

Journal: Neurobiology of disease 20090701

Title: L-Glutamine-induced apoptosis in microglia is mediated by mitochondrial dysfunction.

Journal: The European journal of neuroscience 20090701

Title: Blockade of glutamate release from microglia attenuates experimental autoimmune encephalomyelitis in mice.

Journal: The Tohoku journal of experimental medicine 20090201

Title: Blockade of microglial glutamate release protects against ischemic brain injury.

Journal: Experimental neurology 20081101

Title: Influence of hyaluronan accumulation during cumulus expansion on in vitro porcine oocyte maturation.

Journal: Zygote (Cambridge, England) 20081101

Title: Synthesis of potent water-soluble tissue transglutaminase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20081015

Title: Premature senescence of human endothelial cells induced by inhibition of glutaminase.

Journal: Biogerontology 20080801

Title: Functional and structural characterization of four glutaminases from Escherichia coli and Bacillus subtilis.

Journal: Biochemistry 20080527

Title: Macrophage-induced neurotoxicity is mediated by glutamate and attenuated by glutaminase inhibitors and gap junction inhibitors.

Journal: Life sciences 20080523

Title: Which mechanisms are involved in taurine-dependent granulocytic immune response or amino- and alpha-keto acid homeostasis?

Journal: Amino acids 20080201

Title: Glutamine as a precursor for transmitter glutamate, aspartate and GABA in the cerebellum: a role for phosphate-activated glutaminase.

Journal: Journal of neurochemistry 20080201

Title: [Isolation of Pseudomonas aurantiaca strains capable of overproduction of phenazine antibiotics].

Journal: Mikrobiologiia 20080101

Title: Necrotic neurons enhance microglial neurotoxicity through induction of glutaminase by a MyD88-dependent pathway.

Journal: Journal of neuroinflammation 20080101

Title: Transglutaminase 2 undergoes a large conformational change upon activation.

Journal: PLoS biology 20071201

Title: A tertiary twist to the transglutaminase tale.

Journal: PLoS biology 20071201

Title: Mechanism-of-action determination of GMP synthase inhibitors and target validation in Candida albicans and Aspergillus fumigatus.

Journal: Chemistry & biology 20071001

Title: Perturbations in factor XIII resulting from activation and inhibition examined by solution based methods and detected by MALDI-TOF MS.

Journal: Biochemistry 20070904

Title: Pathways involved in alanyl-glutamine-induced changes in neutrophil amino- and alpha-keto acid homeostasis or immunocompetence.

Journal: Amino acids 20070901

Title: O-linked N-acetylglucosaminyltransferase inhibition prevents G2/M transition in Xenopus laevis oocytes.

Journal: The Journal of biological chemistry 20070427

Title: Influence of hyaluronic acid synthesis and cumulus mucification on bovine oocyte in vitro maturation, fertilisation and embryo development.

Journal: Reproduction, fertility, and development 20070101

Title: y+ LAT-1 mediates transport of the potent and selective iNOS inhibitor, GW274150, in control J774 macrophages.

Journal: Amino acids 20060901

Title: O-linked N-acetylglucosamine suppresses thermal aggregation of Sp1.

Journal: FEBS letters 20060821

Title: Heat induction of heat shock protein 25 requires cellular glutamine in intestinal epithelial cells.

Journal: American journal of physiology. Cell physiology 20060801

Title: Glutamine binding opens the ammonia channel and activates glucosamine-6P synthase.

Journal: The Journal of biological chemistry 20060217

Title: Glutamine in the mechanism of ammonia-induced astrocyte swelling.

Journal: Neurochemistry international 20060101

Title: Glucose-containing peritoneal dialysis fluids regulate leptin secretion from 3T3-L1 adipocytes.

Journal: Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20050701

Title: Differential response of glutamine in cultured neurons and astrocytes.

Journal: Journal of neuroscience research 20050101

Title: Modulation of tumor induced angiogenesis in Ehrlich ascites tumor.

Journal: Journal of experimental & clinical cancer research : CR 20041201

Title: L-Glutamine ameliorates acetaldehyde-induced increase in paracellular permeability in Caco-2 cell monolayer.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20040901

Title: Ammonia neurotoxicity and the mitochondrial permeability transition.

Journal: Journal of bioenergetics and biomembranes 20040801

Title: Androgen secretion by Rcho-1 cells is independent of extracellular glutamate concentration.

Journal: Placenta 20040701

Title: Glutamine-induced free radical production in cultured astrocytes.

Journal: Glia 20040501

Title: A signaling role of glutamine in insulin secretion.

Journal: The Journal of biological chemistry 20040402

Title: Retinal function loss after monocarboxylate transport inhibition.

Journal: Investigative ophthalmology & visual science 20040201

Title: Characterization of the products of the genes SNO1 and SNZ1 involved in pyridoxine synthesis in Saccharomyces cerevisiae.

Journal: European journal of biochemistry 20040201

Title: Mitochondrial glutaminase enhances extracellular glutamate production in HIV-1-infected macrophages: linkage to HIV-1 associated dementia.

Journal: Journal of neurochemistry 20040101

Title: Glutamine stimulates argininosuccinate synthetase gene expression through cytosolic O-glycosylation of Sp1 in Caco-2 cells.

Journal: The Journal of biological chemistry 20031226

Title: High glucose stimulates angiotensinogen gene expression and cell hypertrophy via activation of the hexosamine biosynthesis pathway in rat kidney proximal tubular cells.

Journal: Endocrinology 20031001

Title: Role of acetyl-L-carnitine in the brain: revealed by Bioradiography.

Journal: Biochemical and biophysical research communications 20030711

Title: The active conformation of glutamate synthase and its binding to ferredoxin.

Journal: Journal of molecular biology 20030627

Title: Glutamine delays spontaneous apoptosis in neutrophils.

Journal: American journal of physiology. Cell physiology 20030601

Title: A molecular warhead and its target: tissue transglutaminase and Celiac Sprue.

Journal: Chemistry & biology 20030301

Title: Design, synthesis, and evaluation of gluten peptide analogs as selective inhibitors of human tissue transglutaminase.

Journal: Chemistry & biology 20030301

Title: A novel apoptosis-inducing protein from Helicobacter pylori.

Journal: Molecular microbiology 20030101

Title: Glutamine plays a role in superoxide production and the expression of p47phox, p22phox and gp91phox in rat neutrophils.

Journal: Clinical science (London, England : 1979) 20021001

Title: Localization and possible function of the glutamate transporter, EAAC1, in the rat retina.

Journal: Cell and tissue research 20021001

Title: The hexosamine pathway regulates the plasminogen activator inhibitor-1 gene promoter and Sp1 transcriptional activation through protein kinase C-beta I and -delta.

Journal: The Journal of biological chemistry 20020913

Title: Flux through the hexosamine pathway is a determinant of nuclear factor kappaB- dependent promoter activation.

Journal: Diabetes 20020401

Title: Hexosamines regulate leptin production in 3T3-L1 adipocytes through transcriptional mechanisms.

Journal: Endocrinology 20020101

Title: Properties of glutaminase of crayfish CNS: implications for axon-glia signaling.

Journal: Neuroscience 20020101

Title: gamma-Glutamyltranspeptidase and gamma-glutamyl peptide ligases: fluorophosphonate and phosphonodifluoromethyl ketone analogs as probes of tetrahedral transition state and gamma-glutamyl-phosphate intermediate.

Journal: Methods in enzymology 20020101

Title: Do bacterial L-asparaginases utilize a catalytic triad Thr-Tyr-Glu?

Journal: Biochimica et biophysica acta 20011217

Title: Mechanism for acivicin inactivation of triad glutamine amidotransferases.

Journal: Biochemistry 20010130

Title: Glutamine metabolism to glucosamine is necessary for glutamine inhibition of endothelial nitric oxide synthesis.

Journal: The Biochemical journal 20010115

Title: Stimulation by eicosapentaenoic acids of leptin mRNA expression and its secretion in mouse 3T3-L1 adipocytes in vitro.

Journal: Biochemical and biophysical research communications 20000413

Title: Glucose and streptozotocin stimulate p135 O-glycosylation in pancreatic islets.

Journal: Biochemical and biophysical research communications 20000107

Title: Antiviral effects of 6-diazo-5-oxo-L-norleucin on replication of herpes simplex virus type 1.

Journal: Antiviral research 19970201

Title: Role of glucosamine synthesis in the stimulation of TGF-alpha gene transcription by glucose and EGF.

Journal: The American journal of physiology 19960301

Title: Influence of twenty potentially antiviral substances on in vitro multiplication of hepatitis A virus.

Journal: Antiviral research 19860301

Title: Discriminative effect of gamma-glutamyl transpeptidase inhibitors on metabolism of leukotriene C4 in peritoneal cells.

Journal: Life sciences 19841119

Title: Kulkarni RM, et al. Evaluation of genetic toxicity of 6-diazo-5-oxo-l-norleucine (DON). Toxicol Mech Methods. 2017 Sep;27(7):518-527.

Title: Thangavelu K, et al. Structural basis for the active site inhibition mechanism of human kidney-type glutaminase (KGA). Sci Rep. 2014 Jan 23;4:3827.

Title: Willis RC, et al. The inhibition by 6-diazo-5-oxo-l-norleucine of glutamine catabolism of the cultured human lymphoblast. J Cell Physiol. 1977 Dec;93(3):375-82.

Title: Sharma NS, et al. Targeting tumor-intrinsic hexosamine biosynthesis sensitizes pancreatic cancer to anti-PD1 therapy. J Clin Invest. 2019 Oct 15.

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Tags:157-03-9 Molecular Formula|157-03-9 MDL|157-03-9 SMILES|157-03-9 L-Norleucine, 6-diazo-5-oxo-