1190-49-4 | L-Homocitrulline

Packsize	Purity	Availability	Price	Discounted Price
250mg	98%	in stock	$12.00	$8.00
1g	98%	in stock	$18.00	$12.00
5g	98%	in stock	$85.00	$59.00
10g	98%	in stock	$168.00	$117.00
25g	98%	in stock	$418.00	$292.00

Description

• Catalog Number: AA32213
• Chemical Name: L-Homocitrulline
• CAS Number: 1190-49-4
• Molecular Formula: C7H15N3O3
• Molecular Weight: 189.2123
• MDL Number: MFCD00038143
• SMILES: NC(=O)NCCCC[C@@H](C(=O)O)N

Computed Properties

• Complexity: 184
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Heavy Atom Count: 13
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 4
• Rotatable Bond Count: 6
• XLogP3: -3.9

Upstream Synthesis Route

(S)-2-amino-6-ureidohexanoic acid, commonly known as L-citrulline, is a key compound with versatile applications in chemical synthesis. This amino acid derivative plays a crucial role in various processes, particularly in the production of pharmaceuticals and biochemicals. In chemical synthesis, L-citrulline serves as a valuable building block for creating complex molecules due to its unique structural properties. Its versatile nature allows for the formation of diverse compound structures through different synthetic pathways. Moreover, L-citrulline's presence in the synthesis of peptides and proteins is indispensable, as it acts as a precursor for the formation of arginine, another essential amino acid in the body. Its ability to enhance the efficiency and specificity of various chemical reactions makes it a valuable tool in synthetic chemistry.

Literature

• Simultaneous measurement of protein-bound 3-chlorotyrosine and homocitrulline by LC-MS/MS after hydrolysis assisted by microwave: application to the study of myeloperoxidase activity during hemodialysis.

  Talanta 20120915

• Impact of carbamylation and glycation of collagen type I on migration of HT1080 human fibrosarcoma cells.

  International journal of oncology 20120601

• Quantification of plasma homocitrulline using hydrophilic interaction liquid chromatography (HILIC) coupled to tandem mass spectrometry.

  Analytical and bioanalytical chemistry 20120201

• Potential of Novel EPO Derivatives in Limb Ischemia.

  Cardiology research and practice 20120101

• Impact of premature birth and critical illness on neonatal range of plasma amino acid concentrations determined by LC-MS/MS.

  Molecular genetics and metabolism 20111201

• New device measures atmospheric isocyanic acid.

  Environmental health perspectives 20110801

• Dual mechanism of brain damage induced in vivo by the major metabolites accumulating in hyperornithinemia-hyperammonemia-homocitrullinuria syndrome.

  Brain research 20110119

• Myeloperoxidase-derived oxidation: mechanisms of biological damage and its prevention.

  Journal of clinical biochemistry and nutrition 20110101

• Biological responses to perfluorododecanoic acid exposure in rat kidneys as determined by integrated proteomic and metabonomic studies.

  PloS one 20110101

• Erythropoietin: recent developments in the treatment of spinal cord injury.

  Neurology research international 20110101

• Anticitrulline antibodies can be caused by homocitrulline-containing proteins in rabbits.

  Arthritis and rheumatism 20101101

• Carbamylation-dependent activation of T cells: a novel mechanism in the pathogenesis of autoimmune arthritis.

  Journal of immunology (Baltimore, Md. : 1950) 20100615

• In vitro inhibition of low density lipoprotein carbamylation by vitamins, as an ameliorating atherosclerotic risk in uremic patients.

  Scandinavian journal of clinical and laboratory investigation 20100401

• Evidence that the major metabolites accumulating in hyperornithinemia-hyperammonemia-homocitrullinuria syndrome induce oxidative stress in brain of young rats.

  International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20091101

• Experimental evidence that ornithine and homocitrulline disrupt energy metabolism in brain of young rats.

  Brain research 20090929

• Retinal degeneration.

  Ophthalmology 20090801

• Identification of novel mutations in the SLC25A15 gene in hyperornithinemia-hyperammonemia-homocitrullinuria (HHH) syndrome: a clinical, molecular, and functional study.

  Human mutation 20090501

• Phenotypic variability among patients with hyperornithinaemia-hyperammonaemia-homocitrullinuria syndrome homozygous for the delF188 mutation in SLC25A15.

  Journal of medical genetics 20081101

• 'O', erythropoietin carbamoylation versus carbamylation.

  Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20080901

• Hyperornithinemia-hyperammonemia-homocitrullinuria syndrome (HHH) presenting with acute fulminant hepatic failure.

  Journal of pediatric gastroenterology and nutrition 20080301

• Hyperornithinemia-hyperammonemia-homocitrullinuria syndrome with stroke-like imaging presentation: clinical, biochemical and molecular analysis.

  Journal of the neurological sciences 20080115

• Acetyl-lysine analog peptides as mechanistic probes of protein deacetylases.

  The Journal of biological chemistry 20071221

• Protein carbamylation links inflammation, smoking, uremia and atherogenesis.

  Nature medicine 20071001

• 'Multipurpose oxidase' in atherogenesis.

  Nature medicine 20071001

• Determination of homocitrulline in urine of patients with HHH syndrome by liquid chromatography tandem mass spectrometry.

  Analytical and bioanalytical chemistry 20061201

• HHH syndrome (hyperornithinaemia, hyperammonaemia, homocitrullinuria), with fulminant hepatitis-like presentation.

  Journal of inherited metabolic disease 20060201

• Carbamylated low-density lipoprotein induces death of endothelial cells: a link to atherosclerosis in patients with kidney disease.

  Kidney international 20050701

• Hyperornithinemia, hyperammonemia, and homocitrullinuria syndrome with evidence of mitochondrial dysfunction due to a novel SLC25A15 (ORNT1) gene mutation in a Palestinian family.

  Journal of the neurological sciences 20040315

• The mitochondrial ornithine transporter. Bacterial expression, reconstitution, functional characterization, and tissue distribution of two human isoforms.

  The Journal of biological chemistry 20030829

• Cloning and characterization of human ORNT2: a second mitochondrial ornithine transporter that can rescue a defective ORNT1 in patients with the hyperornithinemia-hyperammonemia-homocitrullinuria syndrome, a urea cycle disorder.

  Molecular genetics and metabolism 20030801

• [Structure-function relationships of mitochondrial transporters].

  Nihon rinsho. Japanese journal of clinical medicine 20020401

• [Mitochondrial ornithine transporter deficiency].

  Nihon rinsho. Japanese journal of clinical medicine 20020401

• Seven novel mutations in the ORNT1 gene (SLC25A15) in patients with hyperornithinemia, hyperammonemia, and homocitrullinuria syndrome.

  Human mutation 20011101

• Clinical and molecular findings in hyperornithinemia-hyperammonemia-homocitrullinuria syndrome.

  Neurology 20010911

• HHH syndrome associated with callosal agenesis and disordered neuronal migration.

  Developmental medicine and child neurology 20010601

• Carbamoylation of glomerular and tubular proteins in patients with kidney failure: a potential mechanism of ongoing renal damage.

  Swiss medical weekly 20010324

• [Hyperornithinemia-hyperammonemia-homocitrullinuria syndrome].

  Ryoikibetsu shokogun shirizu 20010101

• Conscientious metabolic monitoring on a patient with hyperornithinemia-hyperammonemia-homocitrullinuria (HHH) syndrome undergoing anaesthesia.

  Amino acids 20010101