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D(-)-Arginine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

D-Arginine is a chiral resolution reagent to separate racemic compounds into different mirror isomers and is an important tool for the production of optically active drugs.

Category

D-Amino Acids

Catalog number

BAT-003475

CAS number

157-06-2

Molecular Formula

C6H14N4O2

Molecular Weight

174.20

IUPAC Name

(2R)-2-amino-5-(diaminomethylideneamino)pentanoic acid

Synonyms

D-Arg-OH; (R)-2-Amino-5-guanidinopentanoic acid

Appearance

White powder

Purity

99-100% (Assay)

Density

1.2297 g/cm3(rough estimate)

Melting Point

226 °C(dec)

Boiling Point

305.18°C (rough estimate)

Storage

Store at RT

InChI

InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m1/s1

InChI Key

ODKSFYDXXFIFQN-SCSAIBSYSA-N

Canonical SMILES

C(CC(C(=O)O)N)CN=C(N)N

D(-)-Arginine, an enantiomer of the amino acid arginine, boasts a myriad of applications in bioscience. Here are the key applications of D(-)-Arginine articulated with high perplexity and burstiness:

Pharmaceutical Research: Serving as a chiral building block in pharmaceutical synthesis, D(-)-Arginine plays a pivotal role in crafting diverse drug compounds. Its unique stereochemistry exerts influence on the efficacy and safety profiles of medications, prompting researchers to delve into the realm of new therapeutic agents and refine drug formulations for enhanced clinical outcomes.

Nitric Oxide Research: In the domain of nitric oxide studies, D(-)-Arginine takes center stage, particularly in investigations involving nitric oxide synthase (NOS) enzymes. Distinct from its L-enantiomer, D(-)-Arginine acts as a potent NOS inhibitor, offering valuable insights into the roles of nitric oxide in physiological and pathological processes. These studies are indispensable for unraveling the complexities of cardiovascular health, immune responses, and neural signaling pathways.

Metabolic Pathway Analysis: Within metabolic research circles, D(-)-Arginine serves as a cornerstone for exploring arginine metabolism and its implications for cellular functions. By tracing the metabolic destiny of D(-)-Arginine, scientists can unlock profound insights into arginine-associated pathways like the urea cycle and polyamine synthesis. This knowledge fuels advancements in metabolic engineering and informs therapeutic interventions aimed at optimizing cellular functions.

Protein Structure Studies: Stepping into the realm of structural biology, D(-)-Arginine emerges as a key player in elucidating protein-ligand interactions and protein folding phenomena. Leveraging its unique stereochemistry, researchers delve into how proteins recognize and bind to diverse enantiomers, shedding light on the principles of chiral specificity. Such insights are indispensable for driving drug design endeavors and propelling protein engineering initiatives towards new frontiers.

1. D-arginine-loaded metal-organic frameworks nanoparticles sensitize osteosarcoma to radiotherapy.

Chuanchao Du, Bin Zhu, Mengxue Zhou, Yi Hu, Lifo Ruan, Xiaoguang Liu, Jiayu Zhang, Huiru Lu, Fei Jia, Zhifang Chai, Jun Chen. Biomaterials. 2021 Feb; 269: 120642. DOI: 10.1016/j.biomaterials.2020.120642. PMID: 33440291.

Osteosarcoma is a common type of bone cancers with a high rate of pulmonary recurrence. High-dose radiation therapy is useful for the ablation of unresectable osteosarcoma. However, it may cause severe adverse effects. To address this problem, we developed D-arginine-loaded metal-organic frameworks (MOF) nanoparticles for improving the radiosensitivity of osteosarcoma. D-arginine, a metabolically inert enantiomer of L-arginine, could produce nitric oxide and down-regulate hypoxia-inducible factor-1alpha (HIF-1α) to alleviate tumor hypoxia. In addition, MOF could also generate free radicals to kill the tumor cells. Results demonstrate that D-arginine-loaded nanoparticles enhanced tumor ablation and prevented the lung metastasis in mice upon radiation therapy. Furthermore, the nanoparticles or radiation alone had relatively low toxicity in cells and mice. Therefore, D-arginine-loaded MOF nanoparticles are relatively safe and highly effective in sensitizing osteosarcoma to radiotherapy.

2. Amine oxidation by d-arginine dehydrogenase in pseudomonas aeruginosa.

Jacob Ball, Daniel Ouedraogo, Renata A G Reis, Maria Vodovoz, Giovanni Gadda, Archana Iyer. Arch Biochem Biophys. 2017 Oct 15; 632: 192-201. DOI: 10.1016/j.abb.2017.06.013. PMID: 28625766.

d-Arginine dehydrogenase from Pseudomonas aeruginosa (PaDADH) is a flavin-dependent oxidoreductase, which is part of a novel two-enzyme racemization system that functions to convert d-arginine to l-arginine. PaDADH contains a noncovalently linked FAD that shows the highest activity with d-arginine. The enzyme exhibits broad substrate specificity towards d-amino acids, particularly with cationic and hydrophobic d-amino acids. Biochemical studies have established the structure and the mechanistic properties of the enzyme. The enzyme is a true dehydrogenase because it displays no reactivity towards molecular oxygen. As established through solvent and multiple kinetic isotope studies, PaDADH catalyzes an asynchronous CH and NH bond cleavage via a hydride transfer mechanism. Steady-state kinetic studies with d-arginine and d-histidine are consistent with the enzyme following a ping-pong bi-bi mechanism. As shown by a combination of crystallography, kinetic and computational data, the shape and flexibility of loop L1 in the active site of PaDADH are important for substrate capture and broad substrate specificity.

3. Effects of d-arginine on porphyromonas gingivalis biofilm.

Wei-Wei Liu, Qing Cai, Yu-Jie Liu, Hao-Yang Wang, Yu-Yang Li, Wei-Yan Meng, Yan-Qun Liu, Bao-Sheng Li. J Oral Sci. 2020; 62(1): 57-61. DOI: 10.2334/josnusd.19-0075. PMID: 31996524.

Porphyromonas gingivalis (P. gingivalis) is one of the major pathogenic bacteria of periodontitis or peri-implantitis. P. gingivalis tends to attach to the implant's neck with the formation of biofilm, leading to peri-implantitis. d-arginine has been shown to have a potential antimicrobial role. In this study, P. gingivalis was cultured in Brain Heart Infusion broth together with d-arginine. After 3 days (inhibition) or 6 days (dissociation), these were characterized using crystal violet (CV) staining for the biofilm, extracellular polysaccharide (EPS) production from the biofilm, and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay for biofilm activation. Furthermore, the P. gingivalis biofilm was observed by scanning electron microscopy (SEM). d-arginine effectively reduced biomass accumulation and promoted dissociation at concentrations of ≥50 mM and 100 mM, respectively. Through CV staining, d-arginine concentrations of EPS production from the biofilm for inhibition and dissociation effects was ≥50 mM and 100 mM, respectively. In addition, d-arginine affected biofilm activation for the corresponding concentrations: ≥60 mM for inhibition and ≥90 mM for dispersal. Under SEM observation, d-arginine changed the P. gingivalis biofilm structure in relatively high concentrations for inhibition or dissociation, respectively. The authors concluded that d-arginine could inhibit the formation of P. gingivalis biofilm and promote the dissociation of P. gingivalis biofilm.