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156-86-5,MFCD00237108
Catalog No.:AA001OC4

156-86-5 | Homoarginine

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1g
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5g
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25g
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$70.00   $49.00
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100g
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA001OC4
Chemical Name:
Homoarginine
CAS Number:
156-86-5
Molecular Formula:
C7H16N4O2
Molecular Weight:
188.2275
MDL Number:
MFCD00237108
SMILES:
NN=CNCCCC[C@@H](C(=O)O)N
Properties
Computed Properties
 
Complexity:
189  
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:
-3.7  

Upstream Synthesis Route

[1]JournalofNaturalProducts,2012,vol.75,#9,p.1648-1651,4

[2]JournalofNaturalProducts,2012,vol.75,#9,p.1648-1651

[1]JournalofOrganicChemistry,1981,vol.46,#4,p.808-809

Downstream Synthesis Route

[1]ChemicalandPharmaceuticalBulletin,1982,vol.30,p.4435-4443

[1]JournalofOrganicChemistry,1981,vol.46,p.808-809

[1]JournalofOrganicChemistry,1990,vol.55,p.5551-5553

156-86-5    119-53-9   
(S)-2-Amino-6-(4,5-diphenyl-1H-imidazol-2-ylamino)-hexanoicacid 

[1]Chemicalandpharmaceuticalbulletin,1981,vol.29,p.1115-1120

Literature

Title: Homoarginine deficiency is associated with increased bone turnover.

Journal: Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20121101

Title: Promiscuous activity of arginine:glycine amidinotransferase is responsible for the synthesis of the novel cardiovascular risk factor homoarginine.

Journal: FEBS letters 20121019

Title: Nodularin, a cyanobacterial toxin, is synthesized in planta by symbiotic Nostoc sp.

Journal: The ISME journal 20121001

Title: Nicotinic acid adenine dinucleotide phosphate (NAADP) degradation by alkaline phosphatase.

Journal: The Journal of biological chemistry 20120921

Title: Targeting the S1 and S3 subsite of trypsin with unnatural cationic amino acids generates antimicrobial peptides with potential for oral administration.

Journal: Journal of medicinal chemistry 20120726

Title: Simultaneous determination of asymmetric and symmetric dimethylarginine, L-monomethylarginine, L-arginine, and L-homoarginine in biological samples using stable isotope dilution liquid chromatography tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120701

Title: Characterisation of the mgo operon in Pseudomonas syringae pv. syringae UMAF0158 that is required for mangotoxin production.

Journal: BMC microbiology 20120101

Title: Hydroimidazolone modification of the conserved Arg12 in small heat shock proteins: studies on the structure and chaperone function using mutant mimics.

Journal: PloS one 20120101

Title: The mbo operon is specific and essential for biosynthesis of mangotoxin in Pseudomonas syringae.

Journal: PloS one 20120101

Title: Site-specific incorporation of arginine analogs into proteins using arginyl-tRNA synthetase.

Journal: Biochemical and biophysical research communications 20111028

Title: Antimalarial β-carbolines from the New Zealand ascidian Pseudodistoma opacum.

Journal: Journal of natural products 20110923

Title: Chemical and metabolic aspects of antimetabolite toxins produced by Pseudomonas syringae pathovars.

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Title: Low homoarginine concentration is a novel risk factor for heart disease.

Journal: Heart (British Cardiac Society) 20110801

Title: Stable isotope dilution assay for liquid chromatography-tandem mass spectrometric determination of L-homoarginine in human plasma.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110801

Title: Homoarginine, heart failure, and sudden cardiac death in haemodialysis patients.

Journal: European journal of heart failure 20110801

Title: A peptidomic approach for monitoring and characterising peptide cyanotoxins produced in Italian lakes by matrix-assisted laser desorption/ionisation and quadrupole time-of-flight mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20110515

Title: Low serum homoarginine is a novel risk factor for fatal strokes in patients undergoing coronary angiography.

Journal: Stroke 20110401

Title: A look at the brighter facets of β-N-oxalyl-l-α,β-diaminopropionic acid, homoarginine and the grass pea.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20110301

Title: Tissue-nonspecific alkaline phosphatase is activated in enterocytes by oxidative stress via changes in glycosylation.

Journal: Inflammatory bowel diseases 20110201

Title: Bactericidal oncocin derivatives with superior serum stabilities.

Journal: International journal of antimicrobial agents 20110201

Title: Intracellular fates of cell-penetrating block copolypeptide vesicles.

Journal: Biomacromolecules 20110110

Title: The alteration of asymmetric dimetilarginine (ADMA) levels in cardiac and gastrocnemius muscles following radioactive iodine application in guinea pigs and the effect of L-carnitine on this alteration.

Journal: International journal of radiation biology 20110101

Title: Impaired dermal wound healing in discoidin domain receptor 2-deficient mice associated with defective extracellular matrix remodeling.

Journal: Fibrogenesis & tissue repair 20110101

Title: Asymmetric dimethylarginine, endothelial nitric oxide bioavailability and mortality in sepsis.

Journal: PloS one 20110101

Title: Singular features of trypanosomatids' phosphotransferases involved in cell energy management.

Journal: Enzyme research 20110101

Title: Bacterial membrane activity of α-peptide/β-peptoid chimeras: influence of amino acid composition and chain length on the activity against different bacterial strains.

Journal: BMC microbiology 20110101

Title: Quantitation of L-arginine and asymmetric dimethylarginine in human plasma by LC-selective ion mode-MS for Type 2 diabetes mellitus study.

Journal: Chemical & pharmaceutical bulletin 20110101

Title: High-dose siRNAs upregulate mouse Eri-1 at both transcription and posttranscription levels.

Journal: PloS one 20110101

Title: Phosphagen kinases of parasites: unexplored chemotherapeutic targets.

Journal: The Korean journal of parasitology 20101201

Title: Guanidino compounds inhibit acetylcholinesterase and butyrylcholinesterase activities: effect neuroprotector of vitamins E plus C.

Journal: International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20101001

Title: Simultaneous determination of guanidinosuccinic acid and guanidinoacetic acid in urine using high performance liquid chromatography/tandem mass spectrometry.

Journal: Analytica chimica acta 20100916

Title: Homoarginine, cardiovascular risk, and mortality.

Journal: Circulation 20100907

Title: Peptide-peptoid hybrids based on (1-11)-parathyroid hormone analogs.

Journal: Journal of peptide science : an official publication of the European Peptide Society 20100901

Title: Modulatory role of the endogenous nitric oxide synthase inhibitor, asymmetric dimethylarginine (ADMA), in morphine tolerance and dependence in mice.

Journal: Journal of neural transmission (Vienna, Austria : 1996) 20100901

Title: Is homoarginine level associated with high cardiovascular risk and mortality?

Journal: Maedica 20100701

Title: Role of the guanidine group in the N-terminal fragment of PTH(1-11).

Journal: Amino acids 20100401

Title: Toxicity of non-protein amino acids to humans and domestic animals.

Journal: Natural product communications 20100301

Title: Design and synthesis of selective inhibitors of placental alkaline phosphatase.

Journal: Bioorganic & medicinal chemistry 20100115

Title: HPLC analysis of asymmetric dimethylarginine, symmetric dimethylarginine, homoarginine and arginine in small plasma volumes using a Gemini-NX column at high pH.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100101

Title: Guanidino compound levels in blood, cerebrospinal fluid, and post-mortem brain material of patients with argininemia.

Journal: Molecular genetics and metabolism 20100101

Title: Antiproliferative effect of growth hormone-releasing hormone (GHRH) antagonist on ovarian cancer cells through the EGFR-Akt pathway.

Journal: Reproductive biology and endocrinology : RB&E 20100101

Title: Ao38, a new cell line from eggs of the black witch moth, Ascalapha odorata (Lepidoptera: Noctuidae), is permissive for AcMNPV infection and produces high levels of recombinant proteins.

Journal: BMC biotechnology 20100101

Title: Bromopyrrole alkaloids as lead compounds against protozoan parasites.

Journal: Marine drugs 20100101

Title: Mechanisms of catalysis and inhibition operative in the arginine deiminase from the human pathogen Giardia lamblia.

Journal: Bioorganic chemistry 20091001

Title: Ileal digestibility and endogenous flow of minerals and amino acids: responses to dietary phytic acid in piglets.

Journal: The British journal of nutrition 20090801

Title: Evaluation of the furosine and homoarginine methods for determining reactive lysine in rumen-undegraded protein.

Journal: Journal of dairy science 20090801

Title: Structural basis for the erythro-stereospecificity of the L-arginine oxygenase VioC in viomycin biosynthesis.

Journal: The FEBS journal 20090701

Title: Biocompatibility of amphiphilic diblock copolypeptide hydrogels in the central nervous system.

Journal: Biomaterials 20090501

Title: HPLC analysis of asymmetric dimethylarginine (ADMA) and related arginine metabolites in human plasma using a novel non-endogenous internal standard.

Journal: Clinica chimica acta; international journal of clinical chemistry 20090301

Title: Standardized ileal digestibility of reactive lysine in distillers dried grains with solubles fed to growing pigs.

Journal: Journal of agricultural and food chemistry 20090128

Title: Analysis of adenoviral attachment to human platelets.

Journal: Virology journal 20090101

Title: Ric-8A, a Galpha protein guanine nucleotide exchange factor potentiates taste receptor signaling.

Journal: Frontiers in cellular neuroscience 20090101

Title: Serum L-homoarginine concentration is elevated during normal pregnancy and is related to flow-mediated vasodilatation.

Journal: Circulation journal : official journal of the Japanese Circulation Society 20081101

Title: Application of the reactive lysine procedure to estimate lysine digestibility in distillers dried grains with solubles fed to growing pigs.

Journal: Journal of agricultural and food chemistry 20081022

Title: Arginine and methylated arginines in human plasma and urine measured by tandem mass spectrometry without the need for chromatography or sample derivatisation.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20081015

Title: CNS delivery via adsorptive transcytosis.

Journal: The AAPS journal 20080901

Title: Chemical modulation of the chaperone function of human alphaA-crystallin.

Journal: Journal of biochemistry 20080701

Title: The effect of microbial phytase on true and apparent ileal amino acid digestibilities in growing-finishing pigs.

Journal: Journal of animal science 20080701

Title: Knocking down gene expression for growth hormone-releasing hormone inhibits proliferation of human cancer cell lines.

Journal: British journal of cancer 20080603

Title: Photodecomposition of o-phthaldialdehyde-derivatized amino acids by the photodiode array detector during their high-performance liquid chromatographic analysis.

Journal: Journal of chromatography. A 20080328

Title: In vitro modulation of alkaline phosphatase activity of Saccharomyces cerevisiae grown in low or high phosphate medium.

Journal: Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20080101

Title: A novel mutant of the Sup35 protein of Saccharomyces cerevisiae defective in translation termination and in GTPase activity still supports cell viability.

Journal: BMC molecular biology 20080101

Title: Effect of heat damage in an autoclave on the reactive lysine contents of soy products and corn distillers dried grains with solubles. Use of the results to check on lysine damage in common qualities of these ingredients.

Journal: Journal of agricultural and food chemistry 20071226

Title: Simultaneous determination of L-arginine and 12 molecules participating in its metabolic cycle by gradient RP-HPLC method: application to human urine samples.

Journal: Analytica chimica acta 20071219

Title: Mechanism of age-dependent susceptibility and novel treatment strategy in glutaric acidemia type I.

Journal: The Journal of clinical investigation 20071101

Title: Reference values for plasma concentrations of asymmetrical dimethylarginine (ADMA) and other arginine metabolites in men after validation of a chromatographic method.

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Title: High-throughput CZE-UV determination of arginine and dimethylated arginines in human plasma.

Journal: Electrophoresis 20070601

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Title: Synthesis of proteins containing modified arginine residues.

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Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20051215

Title: Determination of methylated arginines by column-switching high-performance liquid chromatography-fluorescence detection.

Journal: The Analyst 20051001

Title: Bacterial cell penetration by beta3-oligohomoarginines: indications for passive transfer through the lipid bilayer.

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Journal: BMC biotechnology 20050101

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Title: Residues determining the binding specificity of uncompetitive inhibitors to tissue-nonspecific alkaline phosphatase.

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Journal: Analytical and bioanalytical chemistry 20041001

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Journal: Archives of pharmacal research 20040101

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Journal: Acta biochimica Polonica 20040101

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Journal: Chemistry & biodiversity 20040101

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Journal: The Journal of biological chemistry 20031121

Title: Comparison of the enzyme-hydrolyzed casein, guanidination, and isotope dilution methods for determining ileal endogenous protein flow in the growing rat and pig.

Journal: Journal of animal science 20031001

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Journal: The Journal of biological chemistry 20030829

Title: Probing of arginine residues in peptides and proteins using selective tagging and electrospray ionization mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20030801

Title: A selective inhibitor of inducible nitric oxide synthase inhibits exhaled breath nitric oxide in healthy volunteers and asthmatics.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20030701

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Journal: Sheng wu hua xue yu sheng wu wu li xue bao Acta biochimica et biophysica Sinica 20030701

Title: L-homoarginine suppresses exocrine pancreas in rats.

Journal: Amino acids 20030601

Title: In vitro effects of L-arginine and guanidino compounds on NTPDase1 and 5'-nucleotidase activities from rat brain synaptosomes.

Journal: International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20030401

Title: Computational docking of L-arginine and its structural analogues to C-terminal domain of Escherichia coli arginine repressor protein (ArgRc).

Journal: Journal of molecular modeling 20030401

Title: A role for guanidino compounds in the brain.

Journal: Molecular and cellular biochemistry 20030201

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Journal: Journal of biochemical and biophysical methods 20030131

Title: Role of nitric oxide in chronic allergen-induced airway cell proliferation and inflammation.

Journal: The Journal of pharmacology and experimental therapeutics 20030101

Title: Screening of substrate analogs as potential enzyme inhibitors for the arginine kinase of Trypanosoma cruzi.

Journal: The Journal of eukaryotic microbiology 20030101

Title: Differences in sialic acid residues among bone alkaline phosphatase isoforms: a physical, biochemical, and immunological characterization.

Journal: Calcified tissue international 20021201

Title: Nitric oxide synthase-mediated phytoalexin accumulation in soybean cotyledons in response to the Diaporthe phaseolorum f. sp. meridionalis elicitor.

Journal: Plant physiology 20021101

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Journal: Experimental eye research 20021101

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Journal: European journal of pharmacology 20020927

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Journal: Journal of peptide science : an official publication of the European Peptide Society 20020701

Title: A prodrug of a selective inhibitor of inducible nitric oxide synthase is neuroprotective in the rat model of glaucoma.

Journal: Journal of glaucoma 20020601

Title: Dehydration modifies guanidino compound concentrations in the different zones of the rat kidney.

Journal: Pflugers Archiv : European journal of physiology 20020501

Title: Synthesis and biological characterization of L-N(6)-(1-iminoethyl)lysine 5-tetrazole-amide, a prodrug of a selective iNOS inhibitor.

Journal: Journal of medicinal chemistry 20020411

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Journal: The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society 20020301

Title: The antiproliferative and immunotoxic effects of L-canavanine and L-canaline.

Journal: Anti-cancer drugs 20020301

Title: Evaluation of the homoarginine technique for measuring true ileal amino acid digestibilities in pigs fed a barley-canola meal-based diet.

Journal: Journal of animal science 20020201

Title: Chemopreventive properties of a selective inducible nitric oxide synthase inhibitor in colon carcinogenesis, administered alone or in combination with celecoxib, a selective cyclooxygenase-2 inhibitor.

Journal: Cancer research 20020101

Title: Investigation of the electrospray response of lysine-, arginine-, and homoarginine-terminal peptide mixtures by liquid chromatography/mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20020101

Title: In vitro stimulation of oxidative stress in cerebral cortex of rats by the guanidino compounds accumulating in hyperargininemia.

Journal: Brain research 20011227

Title: Long-term effect of partial nephrectomy on biological parameters, kidney histology, and guanidino compound levels in mice.

Journal: Metabolism: clinical and experimental 20011201

Title: Purification of the O-glycosylated protein p135 and identification as O-GlcNAc transferase.

Journal: Biochemical and biophysical research communications 20011116

Title: Amino acids in seeds and seedlings of the genus Lens.

Journal: Phytochemistry 20010901

Title: Influence of 72% injury in one kidney on several organs involved in guanidino compound metabolism: a time course study.

Journal: Pflugers Archiv : European journal of physiology 20010701

Title: Multiple transport pathways for dibasic amino acids in the larval midgut of the silkworm Bombyx mori.

Journal: Insect biochemistry and molecular biology 20010427

Title: Isolation and characterization of the gene coding for the amidinotransferase involved in the biosynthesis of phaseolotoxin in Pseudomonas syringae pv. phaseolicola.

Journal: Molecular plant-microbe interactions : MPMI 20010401

Title: Distribution and properties of rat intestinal alkaline phosphatase isoenzymes.

Journal: Experimental animals 20010401

Title: A combination of chemical derivatisation and improved bioinformatic tools optimises protein identification for proteomics.

Journal: Electrophoresis 20010201

Title: Nodularin-Har: a new nodularin from Nodularia.

Journal: Journal of natural products 20010101

Title: L-Canavanine: a higher plant insecticidal allelochemical.

Journal: Amino acids 20010101

Title: Effects of retinoic acid on N-glycosylation and mRNA stability of the liver/bone/kidney alkaline phosphatase in neuronal cells.

Journal: Journal of cellular physiology 20000101

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Title: Atzler D, et al. L-homoarginine and cardiovascular disease. Curr Opin Clin Nutr Metab Care. 2015 Jan;18(1):83-8.

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Tags:156-86-5 Molecular Formula|156-86-5 MDL|156-86-5 SMILES|156-86-5 Homoarginine