L-Homocitrulline
(Synonyms: 高瓜氨酸) 目录号 : GC31587An amino acid and a product of carbamylation
Cas No.:1190-49-4
Sample solution is provided at 25 µL, 10mM.
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- Purity: >98.00%
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- Datasheet
Homocitrulline is an amino acid and a product of carbamylation, a post-translational modification of proteins and amino acids.1,2 It is formed by the adduction of isocyanic acid, a product of urea degradation or thiocyanate oxidation induced by myeloperoxidase (MPO), to the ε-amino group of lysine residues.2 Protein-bound homocitrulline levels are increased in the aortas of transgenic Ldlr-/- mice expressing human MPO fed a high-fat atherogenic diet.3 Intra-articular injection of homocitrulline-containing peptides induce the development of arthritis in mice.4 Homocitrulline-containing peptide and anti-homocitrulline antibody levels are increased in whole blood from patients with erosive rheumatoid arthritis compared to patients with non-erosive rheumatoid arthritis.
1.Shi, J., Knevel, R., Suwannalai, P., et al.Autoantibodies recognizing carbamylated proteins are present in sera of patients with rheumatoid arthritis and predict joint damageProc. Natl. Acad. Sci. USA108(42)17372-17377(2011) 2.Verbrugge, F.H., Tang, W.H.W., and Hazen, S.L.Protein carbamylation and cardiovascular diseaseKidney Int.88(3)474-478(2015) 3.Wang, Z., Nicholls, S.J., Rodriquez, E.R., et al.Protein carbamylation links inflammation, smoking, uremia and atherogenesisNat. Med.13(1)1176-1184(2007) 4.Mydel, P., Wang, Z., Brisslert, M., et al.Carbamylation-dependent activation of T cells: A novel mechanism in the pathogenesis of autoimmune arthritisJ. Immunol.184(12)6882-6890(2010)
Cas No. | 1190-49-4 | SDF | |
别名 | 高瓜氨酸 | ||
Canonical SMILES | [H][C@](N)(CCCCNC(N)=O)C(O)=O | ||
分子式 | C7H15N3O3 | 分子量 | 189.21 |
溶解度 | H2O : 33.33 mg/mL (176.15 mM; ultrasonic and warming and heat to 60°C); DMSO : < 1 mg/mL (insoluble or slightly soluble) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 5.2851 mL | 26.4257 mL | 52.8513 mL |
5 mM | 1.057 mL | 5.2851 mL | 10.5703 mL |
10 mM | 0.5285 mL | 2.6426 mL | 5.2851 mL |
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2.
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Absorption of homocitrulline from the gastrointestinal tract
1. Transport of L-homocitrulline, an amino acid which occurs in milk products, was studied with rat small intestine in vitro and from the human mouth in vivo. Absorption was partially dependent, in both systems, on the presence of sodium ions. 2. Metabolic inhibitors decreased L-homocitrulline uptake across the small intestine. Transport across the intestine did not occur against the concentration gradient but did show saturation kinetics. 3. The barbiturate, amytal, did not inhibit buccal absorption. Saturation kinetics were demonstrated. 4. Experiments were conducted with L-citrulline, or other amino acids, as possible inhibitors of L-homocitrulline transport. Results were compatible with Na+-dependent carrier-mediated uptake across the buccal mucosa. Active transport could be involved with the small intestine assuming that L-homocitrulline has a low affinity for the carrier system.
Identification of a new metabolite of L-homocitrulline
Metabolism of L-homocitrulline by a mouse liver enzyme
Serum metabolomic profiling reveals an increase in homocitrulline in Chinese patients with nonalcoholic fatty liver disease: a retrospective study
Backgrounds: Nonalcoholic fatty liver disease (NAFLD) has multiple causes, is triggered by individual genetic susceptibility, environmental factors, and metabolic disturbances, and may be triggered by acquired metabolic stress. The metabolic profiles of NAFLD show significant ethnic differences, and the metabolic characteristics of NAFLD in Chinese individuals are unclear. Our study aimed to identify the metabolites and pathways associated with NAFLD in a Chinese cohort.
Methods: One hundred participants, including 50 NAFLD patients and 50 healthy controls, were enrolled in this retrospective observational study at Jinling Hospital in Nanjing; serum samples were collected from the patients and healthy subjects. The metabolome was determined in all samples by liquid chromatography-hybrid quadrupole time-of-flight mass spectrometry (LC-Q/TOF-MS). Univariate and multivariate statistical analyses were used to compare the metabolic profiles between the two groups.
Results: The comparison indicated that the levels of 89 metabolites were different between the two groups. The glycerophospholipid family of metabolites was the most abundant family of metabolites that demonstrated significant differences. L-acetylcarnitine, L-homocitrulline, and glutamic acid were the top three metabolites ranked by VIP score and had favorable effective functions for diagnosis. Moreover, pathway enrichment analysis suggested 14 potentially different metabolic pathways between NAFLD patients and healthy controls based on their impact value. Biological modules involved in the lipid and carbohydrate metabolism had the highest relevance to the conditions of NAFLD. Glycerophospholipid metabolism had the strongest associations with the conditions of NAFLD.
Conclusions: Our data suggest that the serum metabolic profiles of NAFLD patients and healthy controls are different. L-Homocitrulline was remarkably increased in NAFLD patients.