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Chemical Structure| 74-79-3 Chemical Structure| 74-79-3
Chemical Structure| 74-79-3

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CAS No.: 74-79-3

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L-Arginine is the nitrogen donor for synthesis of nitric oxide, a potent vasodilator that is deficient during times of sickle cell crisis.

Synonyms: (S)-(+)-Arginine; L-Arginine

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Product Citations      Show More

Reynolds, Donald L ; Simpson, E Barry ; Hille, Matthew M ;

Abstract: Enterococcus faecalis (E. faecalis) is a ubiquitous microbe occurring in the environment and in the intestinal tract of poultry. E. faecalis has been identified in cases of egg infertility and/or decreased hatchability and can cause amyloid arthropathy in older laying chickens. E. faecalis produces cytolysin, a bacterial exotoxin that can cause lysis of erythrocytes. It has been difficult to demonstrate this virulence trait using conventional culture methods with sheep blood agar. A 96-well microplate hemolysis assay, along with a culture method incorporating glucose and L-arginine into the culture media, is described that demonstrates the production of cytolysin in E. faecalis isolates of avian origin. Additionally, the results show that horse and sheep erythrocytes were susceptible to lysis by the E. faecalis cytolysin, but cow and chicken erythrocytes were less susceptible.

Keywords: Enterococcus faecalis ; hemolysis ; cytolysin ; avian

Purchased from AmBeed: ;

Hyung Shik Kim ; Elias A. Halabi ; Noah Enbergs ; Rainer H. Kohler ; Fan Fei ; Christopher S. Garris , et al.

Abstract: Rationale: constructs are commonly used for vaccination, immune stimulation, and gene therapy, but their use in cancer still remains limited. One of the reasons is that systemic delivery to tumor-associated antigen-presenting cells (dendritic cells and macrophages) is often inefficient, while off-target nucleic acid-sensing immune pathways can stimulate systemic immune responses. Conversely, certain carbohydrate nanoparticles with small molecule payloads have been shown to target these cells efficiently in the tumor microenvironment. Yet, incorporation into such carbohydrate-based nanoparticles has proven challenging. Methods: We developed a novel approach using cross-linked bis succinyl-cyclodextrin (b-s-CD) nanoparticles to efficiently deliver nucleic acids and small-molecule immune enhancer to phagocytic cells in tumor environments and lymph nodes. Our study involved incorporating these components into the nanoparticles and assessing their efficacy in activating antigen-presenting cells. Results: The multi-modality immune stimulators effectively activated antigen-presenting cells and promoted immunity in vivo. This was evidenced by enhanced delivery to phagocytic cells and subsequent immune response activation in tumor environments and lymph nodes. Conclusion: Here, we describe a new approach to incorporating both nucleic acids and small-molecule immune enhancers into cross-linked bis succinyl-cyclodextrin (b-s-CD) nanoparticles for efficient delivery to phagocytic cells in tumor environments and lymph nodes in vivo. These multi-modality immune stimulators can activate antigen-presenting cells and foster immunity. We argue that this strategy can potentially be used to enhance efficacy.

Keywords: delivery ; nanoparticles ; dendritic cells ; vaccine ; cancer ; lymph node

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Calabretta, Lindsey O. ; Yang, Jinyi ; Raines, Ronald T. ;

Abstract: The field of cell-penetrating peptides is dominated by the use of oligomers of arginine residues. Octanol-water partitioning in the presence of an anionic lipid is a validated proxy for cell-penetrative efficacy. Here, we add one, two, or three N-Me groups to Ac-Arg-NH2 and examine the effects on octanol-water partitioning. In the absence of an anionic lipid, none of these arginine derivatives can be detected in the octanol layer. In the presence of sodium dodecanoate, however, increasing N-methylation correlates with increasing partitioning into octanol, which is predictive of higher cell-penetrative ability. We then evaluated fully Nα-methylated oligoarginine peptides and observed an increase in their cellular penetration compared with canonical oligoarginine peptides in some contexts. These findings indicate that a simple modification, Nα-methylation, can enhance the performance of cell-penetrating peptides.

Keywords: guanidino group ; octanol-water partitioning ; peptoid ; topological polar surface area

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Alternative Products

Product Details of H-Arg-OH

CAS No. :74-79-3
Formula : C6H14N4O2
M.W : 174.20
SMILES Code : O=C(O)[C@@H](N)CCCNC(N)=N
Synonyms :
(S)-(+)-Arginine; L-Arginine
MDL No. :MFCD00002635

Safety of H-Arg-OH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of H-Arg-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 74-79-3 ]

[ 74-79-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 67-56-1 ]
  • [ 74-79-3 ]
  • [ 22888-59-1 ]
  • 2
  • [ 74-79-3 ]
  • [ 72040-64-3 ]
  • (S)-5-Guanidino-2-{6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoylamino}-pentanoic acid [ No CAS ]
  • 3
  • [ 74-79-3 ]
  • [ 1119-34-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In 1,4-dioxane; General procedure: TLC plates were purchased from Merck KGaA, Millipore Corporation. Flash Column Chromatography performed using silica gel from Sorbent Technologies in Chemglass fritted columns. Silica Dimensions: porosity 60 A, particle size: 40-63 mm, 230 x 400 mesh. Preparative HPLC performed on a Gilson PLC 2020. Column: Synergi 4m Fusion-RP by Phenomenex, 150 x 21.2 mm. Elution performed with a step gradient of 5% CH3CN in H2O for 5 min followed by a ramp to 1:1 CH3CN/H2O over 12 min (no buffers were used) at 20 mL/min flow rate. Compounds dissolved in 0.1% aq. formic acid with 10-20% CH3CN added as needed for solubility. Solutions were concentrated on a Buchi Rotovapor R-210 with Chemglass fritted adapters. Compounds purified by HPLC or from Stability Studies (below) were concentrated by lyophilization using a Labconco Freezone 2.5 Plus. Analytical HPLC for purity determination was performed on a Waters system (1525 Binary Pump and 2487 Dual l Absorbance Detector). Column: Synergi 4m Fusion-RP by Phenomenex, 150 x 4.6 mm. Isocratic elution performed with 0 or 5% CH3CN in 0.1% aq. formic acid at 0.5 mL/min or 1.0 mL/min flow rate. Compounds were dissolved in 0.1% aq. formic acid for HPLC analysis. Glassware was dried while under high vacuum using a heat gun by Varitemp, Master Appliance Corp. (Model: Vt-750C) to heat glassware to >150 C and then charged with Ar. High vacuum from Thomas Industries Inc. (Welch Model 1400B-01, Serial EE121257). 1H and 13CNMR were recorded on a Bruker instrument operating at 300 and 75 MHz, respectively. NMR spectra were obtained as CDCl3, CD3OD, and (CD3)2SO solutions (reported in ppm), using residual solvent peaks in the 1H and 13C NMR spectra (CDCl3: 7.27, 77.23 ppm; CD3OD: 3.31, 49.15 ppm; and (CD3)2SO: 2.50, 39.51 ppm) as the reference standard, respectively. All J values are given in units of Hz. Reagents were purchased from commercial suppliers such as Sigma-Aldrich, Acros Organics, Fisher Scientific, Astatech, Wilmad LabGlass, and Pharmco-Aaper which were used without further purification. Anhydrous MeOH, DME, DMF and THF were purchased from EMD Chemicals (Drisolv line). Optical rotations were measured on a Rudolph Research Autopol III polarimeter (using sodium D line, 589 nm) and [alpha]D given in units of (degrees-mL)/(dm-g), and concentration (c) is reported in units of g/100 mL. HRMS analysis (TOF ES+) was performed on a Micromass Q-Tof Ultimamass spectrometer. pKa values were determined at Analiza using a pKa PRO Analyzer (AATI, Ames, IA), as follows: An electrophoretic separation was performed in parallel across 24 different pH values. The compounds were detected by UV at 214 nm. The average pH spacing between buffer points was 0.4 pH units (pH range of 1.7-11.2). Four consecutive capillary electrophoresis runs were performed for each compound. Norfloxacin was used as a standard. The total number of pKa values was predicted by relating mobility andcompound molecular weight using pKa Estimator software (AATI, Ames, IA). Melting points were obtained using a Mel-Temp apparatus and are uncorrected. Sonication was performed using a VWR Aquasonic Model 75T. Amino acid controls L-leucine, L-phenylalanine, L-arginine, L-tyrosine, L-tryptophan, L-glycine, L-isoleucine, and L-methionine were purchased from commercial suppliers and converted to their HCl salts (by suspension in dioxane and addition of 1.05 equiv. of 4N HCl in dioxane, followed by concentration in vacuo) prior to testing in cell assays. Gly-HA 12h was purchased from Alfa Chemistry.
  • 4
  • [ 74-79-3 ]
  • [ 134395-00-9 ]
  • atorvastatin arginine [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.9% In methanol; for 8h;Reflux; The preparation method of atorvastatin arginine salt comprises the following steps: Atorvastatin tert-butyl ester 10g, 70mL anhydrous methanol in the250mL of three bottles, stirring at room temperature;5 mL was added dropwiseConcentrated hydrochloric acid PH 1, stirring at room temperature, a few minutes after the solution clear and transparent, the process of TLC detection (chloroform: methanol = 50: 1), an hour later, the reaction is completed. The reaction bottle placed in ice bath, with 5mol / L NaOH solution alkali rho Eta = 13-14, 3h after the reaction is completed,The methanol in the reaction mixture was removed by rotary evaporation, and the remaining residue was poured into 100 mL of water,The suspension was washed with 100 mL of X2 methyl tert-butyl ether.Methyl tert-butyl ether was removed and removed, The remaining water was acidified with 1 mol / L HC1 solution to pH = 3-4 and the solution was extracted with 80 mL of ethyl acetate The separated organic phase was adjusted to rho H = 6-7 with a saturated solution of 110) 3, and a small amount of water was separated off and the organic phase was separated Saturated sodium chloride solution 40mL washed once, anhydrous sodium sulfate drying 2h, steamed to remove ethyl acetate,To give atorvastatin acid 7. 5 g. The resulting 7. 5 g of atorvastatin acid was mixed with 30 mL of anhydrous methanol, 4. 7 g of L-arginine, and 5 mL of waterDissolved in three bottles, heated to reflux 8h 5)The solvent was removed by rotary evaporation, dried in vacuo for 2 h, and dried in 50 mL of anhydrous methanol. The solid was removed by filtration, Acid, repeated five times, steam to remove methanol, the residue dried with vacuum oil chestnut 2h, atorvastatin arginine salt 7. 2gThe atorvastatin arginine salt yield in this example was 72.9%.
 

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