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1188-37-0,MFCD00002802
Catalog No.:AA0080QI

1188-37-0 | N-Acetyl-l-glutamic acid

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Purity
Availability
Price(USD)
Quantity
  
25g
98%
in stock  
$19.00   $14.00
- +
100g
98%
in stock  
$36.00   $25.00
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500g
98%
in stock  
$173.00   $121.00
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
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  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0080QI
Chemical Name:
N-Acetyl-l-glutamic acid
CAS Number:
1188-37-0
Molecular Formula:
C7H11NO5
Molecular Weight:
189.1659
MDL Number:
MFCD00002802
SMILES:
OC(=O)CC[C@@H](C(=O)O)NC(=O)C
FEMA Number:
4752
Properties
Computed Properties
 
Complexity:
225  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
5  
XLogP3:
-1.8  

Upstream Synthesis Route

[1]ChemischeBerichte,1930,vol.63,p.438

[2]JournalofBiologicalChemistry,1940,vol.132,p.165

[1]SyntheticCommunications,1992,vol.22,#2,p.257-264

[2]ChemistryofHeterocyclicCompounds(NewYork,NY,UnitedStates),1995,vol.31,#1,p.33-34

[3]KhimiyaGeterotsiklicheskikhSoedinenii,1995,#1,p.39-41

[4]ChemicalPapers,2011,vol.65,#1,p.70-76

[1]CellChemicalBiology,2016,vol.23,#8,p.935-945

[1]JournaloftheAmericanChemicalSociety,2009,vol.131,#32,p.11323-11325

[1]ChemischeBerichte,1930,vol.63,p.438

[2]JournalofBiologicalChemistry,1940,vol.132,p.165

Downstream Synthesis Route

[1]Hoppe-Seyler'sZeitschriftfurPhysiologischeChemie,1940,vol.265,p.31,37

[2]CarbohydrateResearch,1976,vol.47,p.49-61

[1]ChemischeBerichte,1930,vol.63,p.438

[1]ChemischeBerichte,1930,vol.63,p.438

[1]AustralianJournalofScientificResearch,SeriesA:PhysicalSciences,1952,vol.5,p.728,732

[1]JournaloftheChemicalSociety,1958,p.3283,3286

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Title: A novel bifunctional N-acetylglutamate synthase-kinase from Xanthomonas campestris that is closely related to mammalian N-acetylglutamate synthase.

Journal: BMC biochemistry 20070101

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Journal: BMC genomics 20070101

Title: Expression, crystallization and preliminary crystallographic studies of a novel bifunctional N-acetylglutamate synthase/kinase from Xanthomonas campestris homologous to vertebrate N-acetylglutamate synthase.

Journal: Acta crystallographica. Section F, Structural biology and crystallization communications 20061201

Title: Mapping active site residues in glutamate-5-kinase. The substrate glutamate and the feed-back inhibitor proline bind at overlapping sites.

Journal: FEBS letters 20061113

Title: A metabonomics study of the hepatotoxicants galactosamine, methylene dianiline and clofibrate in rats.

Journal: Basic & clinical pharmacology & toxicology 20060901

Title: Tight binding inhibitors of N-acyl amino sugar and N-acyl amino acid deacetylases.

Journal: Journal of the American Chemical Society 20060405

Title: The regulatory PII protein controls arginine biosynthesis in Arabidopsis.

Journal: FEBS letters 20060403

Title: Changes in flagellin glycosylation affect Campylobacter autoagglutination and virulence.

Journal: Molecular microbiology 20060401

Title: Agmatine stimulates hepatic fatty acid oxidation: a possible mechanism for up-regulation of ureagenesis.

Journal: The Journal of biological chemistry 20060331

Title: The PII signal transduction protein of Arabidopsis thaliana forms an arginine-regulated complex with plastid N-acetyl glutamate kinase.

Journal: The Journal of biological chemistry 20060303

Title: Biochemical properties of recombinant human and mouse N-acetylglutamate synthase.

Journal: Molecular genetics and metabolism 20060301

Title: Structural bases of feed-back control of arginine biosynthesis, revealed by the structures of two hexameric N-acetylglutamate kinases, from Thermotoga maritima and Pseudomonas aeruginosa.

Journal: Journal of molecular biology 20060224

Title: [Cloning, sequence analysis and expression of N-acetylglutamate kinase gene in Corynebacterium crenatum].

Journal: Wei sheng wu xue bao = Acta microbiologica Sinica 20060201

Title: Expression of ornithine-urea cycle enzymes in early life stages of air-breathing walking catfish Clarias batrachus and induction of ureogenesis under hyper-ammonia stress.

Journal: Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20060101

Title: Bioinformatic analysis of an unusual gene-enzyme relationship in the arginine biosynthetic pathway among marine gamma proteobacteria: implications concerning the formation of N-acetylated intermediates in prokaryotes.

Journal: BMC genomics 20060101

Title: Stationary phase expression of the arginine biosynthetic operon argCBH in Escherichia coli.

Journal: BMC microbiology 20060101

Title: The dogfish shark (Squalus acanthias) increases both hepatic and extrahepatic ornithine urea cycle enzyme activities for nitrogen conservation after feeding.

Journal: Physiological and biochemical zoology : PBZ 20060101

Title: Increases in urea synthesis and the ornithine-urea cycle capacity in the giant African snail, Achatina fulica, during fasting or aestivation, or after the injection with ammonium chloride.

Journal: Journal of experimental zoology. Part A, Comparative experimental biology 20051201

Title: Harnessing natural diversity to probe metabolic pathways.

Journal: PLoS genetics 20051201

Title: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism.

Journal: Clinical biochemistry 20051101

Title: Purification and characterization of glutamate N-acetyltransferase involved in citrulline accumulation in wild watermelon.

Journal: The FEBS journal 20051001

Title: The crystal structure of Pyrococcus furiosus UMP kinase provides insight into catalysis and regulation in microbial pyrimidine nucleotide biosynthesis.

Journal: Journal of molecular biology 20050916

Title: N-acetyl glutamate kinase from Daucus carota suspension cultures: embryogenic expression profile, purification and characterization.

Journal: Plant physiology and biochemistry : PPB 20050901

Title: Acupuncture treatment for 15 cases of post-traumatic coma.

Journal: Journal of traditional Chinese medicine = Chung i tsa chih ying wen pan 20050901

Title: Efficient complexation of N-acetyl amino acid carboxylates in water by an artificial receptor: unexpected cooperativity in the binding of glutamate but not aspartate.

Journal: Journal of the American Chemical Society 20050803

Title: Genes, enzymes and regulation of arginine biosynthesis in plants.

Journal: Plant physiology and biochemistry : PPB 20050801

Title: Understanding carbamoyl phosphate synthetase deficiency: impact of clinical mutations on enzyme functionality.

Journal: Journal of molecular biology 20050527

Title: The role of mitochondrially bound arginase in the regulation of urea synthesis: studies with [U-15N4]arginine, isolated mitochondria, and perfused rat liver.

Journal: The Journal of biological chemistry 20050506

Title: Identification of novel mutations of the human N-acetylglutamate synthase gene and their functional investigation by expression studies.

Journal: Biochimica et biophysica acta 20050415

Title: Role of N-acetylglutamate turnover in urea synthesis of rats given proteins of different quality.

Journal: Journal of nutritional science and vitaminology 20050401

Title: Unusual reactivity in a commercial chromium supplement compared to baseline DNA cleavage with synthetic chromium complexes.

Journal: Journal of inorganic biochemistry 20050301

Title: Late onset N-acetylglutamate synthase deficiency caused by hypomorphic alleles.

Journal: Human mutation 20050301

Title: A comprehensive update of the sequence and structure classification of kinases.

Journal: BMC structural biology 20050101

Title: The little skate Raja erinacea exhibits an extrahepatic ornithine urea cycle in the muscle and modulates nitrogen metabolism during low-salinity challenge.

Journal: Physiological and biochemical zoology : PBZ 20050101

Title: N-carbamylglutamate protects patients with decompensated propionic aciduria from hyperammonaemia.

Journal: Journal of inherited metabolic disease 20050101

Title: Complex formation and catalytic activation by the PII signaling protein of N-acetyl-L-glutamate kinase from Synechococcus elongatus strain PCC 7942.

Journal: The Journal of biological chemistry 20041231

Title: Interaction of N-acetylglutamate kinase with a PII-like protein in rice.

Journal: Plant & cell physiology 20041201

Title: The Synechococcus elongatus P signal transduction protein controls arginine synthesis by complex formation with N-acetyl-L-glutamate kinase.

Journal: Molecular microbiology 20040601

Title: Urea synthesis by ruminal epithelial and duodenal mucosal cells from growing sheep.

Journal: Journal of dairy science 20040601

Title: Dogmas and controversies in the handling of nitrogenous wastes: ureotely and ammonia tolerance in early life stages of the gulf toadfish, Opsanus beta.

Journal: The Journal of experimental biology 20040501

Title: Dogmas and controversies in the handling of nitrogenous wastes: osmoregulation during early embryonic development in the marine little skate Raja erinacea; response to changes in external salinity.

Journal: The Journal of experimental biology 20040501

Title: Mammalian N-acetylglutamate synthase.

Journal: Molecular genetics and metabolism 20040401

Title: Carglumic acid: new preparation. An advance in rare urea cycle disorders.

Journal: Prescrire international 20040201

Title: Recent advances in arginine metabolism.

Journal: Current opinion in clinical nutrition and metabolic care 20040101

Title: Characteristics of prolinase against various iminodipeptides in erythrocyte lysates from a normal human and a patient with prolidase deficiency.

Journal: Clinical chemistry and laboratory medicine 20040101

Title: Site-directed mutagenesis of Escherichia coli acetylglutamate kinase and aspartokinase III probes the catalytic and substrate-binding mechanisms of these amino acid kinase family enzymes and allows three-dimensional modelling of aspartokinase.

Journal: Journal of molecular biology 20031128

Title: Role of the glutamate dehydrogenase reaction in furnishing aspartate nitrogen for urea synthesis: studies in perfused rat liver with 15N.

Journal: The Biochemical journal 20031115

Title: Hyperammonaemia as a cause of psychosis in an adolescent.

Journal: European journal of pediatrics 20031101

Title: Straightforward relative quantitation and age-related human standards of N-acetylaspartate at the centrum semiovale level by CSI (1)H-MRS.

Journal: Magnetic resonance imaging 20031101

Title: Urea synthesis in the African lungfish Protopterus dolloi--hepatic carbamoyl phosphate synthetase III and glutamine synthetase are upregulated by 6 days of aerial exposure.

Journal: The Journal of experimental biology 20031001

Title: A comparison of the effects of environmental ammonia exposure on the Asian freshwater stingray Himantura signifer and the Amazonian freshwater stingray Potamotrygon motoro.

Journal: The Journal of experimental biology 20031001

Title: The osmotic response of the Asian freshwater stingray (Himantura signifer) to increased salinity: a comparison with marine (Taeniura lymma) and Amazonian freshwater (Potamotrygon motoro) stingrays.

Journal: The Journal of experimental biology 20030901

Title: UMP kinase from the Gram-positive bacterium Bacillus subtilis is strongly dependent on GTP for optimal activity.

Journal: European journal of biochemistry 20030801

Title: The course of phosphorus in the reaction of N-acetyl-L-glutamate kinase, determined from the structures of crystalline complexes, including a complex with an AlF(4)(-) transition state mimic.

Journal: Journal of molecular biology 20030801

Title: N-carbamylglutamate enhances ammonia detoxification in a patient with decompensated methylmalonic aciduria.

Journal: Molecular genetics and metabolism 20030801

Title: N-acetylglutamate and its changing role through evolution.

Journal: The Biochemical journal 20030601

Title: Mutation analysis in patients with N-acetylglutamate synthase deficiency.

Journal: Human mutation 20030601

Title: Null mutations in the N-acetylglutamate synthase gene associated with acute neonatal disease and hyperammonemia.

Journal: Human genetics 20030401

Title: The N-acetylglutamate synthase/N-acetylglutamate kinase metabolon of Saccharomyces cerevisiae allows co-ordinated feedback regulation of the first two steps in arginine biosynthesis.

Journal: European journal of biochemistry 20030301

Title: Cloning and expression of the human N-acetylglutamate synthase gene.

Journal: Biochemical and biophysical research communications 20021213

Title: Role of N-acetylglutamate concentration and ornithine transport into mitochondria in urea synthesis of rats given proteins of different quality.

Journal: Journal of agricultural and food chemistry 20021204

Title: Regulation of urea synthesis by agmatine in the perfused liver: studies with 15N.

Journal: American journal of physiology. Endocrinology and metabolism 20021201

Title: N-acetylglutamate synthase deficiency and the treatment of hyperammonemic encephalopathy.

Journal: Annals of neurology 20021201

Title: Hyperammonemia in carnitine-deficient adult JVS mice used by starvation.

Journal: Metabolic brain disease 20021201

Title: A crystallographic glimpse of a nucleotide triphosphate (AMPPNP) bound to a protein surface: external and internal AMPPNP molecules in crystalline N-acetyl-L-glutamate kinase.

Journal: Acta crystallographica. Section D, Biological crystallography 20021001

Title: A radiometric assay for aspartoacylase activity in cultured oligodendrocytes.

Journal: Analytical biochemistry 20020915

Title: Enantioseparation of amino acid derivatives by capillary zone electrophoresis using vancomycin as chiral selector.

Journal: Electrophoresis 20020901

Title: Identification, cloning and expression of the mouse N-acetylglutamate synthase gene.

Journal: The Biochemical journal 20020615

Title: Towards structural understanding of feedback control of arginine biosynthesis: cloning and expression of the gene for the arginine-inhibited N-acetyl-L-glutamate kinase from Pseudomonas aeruginosa, purification and crystallization of the recombinant enzyme and preliminary X-ray studies.

Journal: Acta crystallographica. Section D, Biological crystallography 20020601

Title: Hepatic glutaminase--a special role in urea synthesis?

Journal: Nutrition (Burbank, Los Angeles County, Calif.) 20020601

Title: ORF6 from the clavulanic acid gene cluster of Streptomyces clavuligerus has ornithine acetyltransferase activity.

Journal: European journal of biochemistry 20020401

Title: Structure of acetylglutamate kinase, a key enzyme for arginine biosynthesis and a prototype for the amino acid kinase enzyme family, during catalysis.

Journal: Structure (London, England : 1993) 20020301

Title: Nitrogen metabolism and excretion in the mangrove killifish Rivulus marmoratus II. Significant ammonia volatilization in a teleost during air-exposure.

Journal: The Journal of experimental biology 20020101

Title: N-acetyl-glutamate synthetase deficiency or porto-systemic shunt associated encephalopathy?

Journal: Acta paediatrica (Oslo, Norway : 1992) 20020101

Title: A new yeast metabolon involving at least the two first enzymes of arginine biosynthesis: acetylglutamate synthase activity requires complex formation with acetylglutamate kinase.

Journal: The Journal of biological chemistry 20011116

Title: Effects of exercise on nitrogen excretion, carbamoyl phosphate synthetase III activity and related urea cycle enzymes in muscle and liver tissues of juvenile rainbow trout (Oncorhynchus mykiss).

Journal: Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20010601

Title: Ammonia detoxification and localization of urea cycle enzyme activity in embryos of the rainbow trout (Oncorhynchus mykiss) in relation to early tolerance to high environmental ammonia levels.

Journal: The Journal of experimental biology 20010601

Title: Pathways for urea production during early life of an air-breathing teleost, the African catfish Clarias gariepinus Burchell.

Journal: The Journal of experimental biology 20010601

Title: Conservation of the binding site for the arginine repressor in all bacterial lineages.

Journal: Genome biology 20010101

Title: M Hashimoto, et al. Animal cell culturing media containing N-acetyl-L-glutamic acid. Patent.

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Tags:1188-37-0 Molecular Formula|1188-37-0 MDL|1188-37-0 SMILES|1188-37-0 N-Acetyl-l-glutamic acid