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Nα,Nω,Nω'-Tris-Z-L-arginine

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

Category

CBZ-Amino Acids

Catalog number

BAT-003199

CAS number

14611-34-8

Molecular Formula

C30H32N4O8

Molecular Weight

576.60

IUPAC Name

(2S)-2-(phenylmethoxycarbonylamino)-5-[phenylmethoxycarbonyl-(N-phenylmethoxycarbonylcarbamimidoyl)amino]pentanoic acid

Synonyms

Z-L-Arg(Z)2-OH; Z-ARG(DI-Z)-OH; Tris(carbobenzoxy)-L-arginine; tris-Z-arginine; TRI-CBZ-L-ARGININE; CBZ-ARG(CBZ)2-OH

Appearance

White to off-white powder

Purity

≥ 98% (HPLC)

Density

1.27±0.1 g/cm3

Melting Point

124-144 °C

Storage

Store at 2-8 °C

InChI

InChI=1S/C30H32N4O8/c31-27(33-29(38)41-20-23-13-6-2-7-14-23)34(30(39)42-21-24-15-8-3-9-16-24)18-10-17-25(26(35)36)32-28(37)40-19-22-11-4-1-5-12-22/h1-9,11-16,25H,10,17-21H2,(H,32,37)(H,35,36)(H2,31,33,38)/t25-/m0/s1

InChI Key

YSGAXJCIEJGVFV-VWLOTQADSA-N

Canonical SMILES

C1=CC=C(C=C1)COC(=O)NC(CCCN(C(=NC(=O)OCC2=CC=CC=C2)N)C(=O)OCC3=CC=CC=C3)C(=O)O

Nα,Nω,Nω'-Tris-Z-L-arginine, a derivative of the amino acid L-arginine, plays a pivotal role in various biochemical and pharmacological research domains. Discover the key applications of this compound, presented with a high degree of perplexity and burstiness:

Enzyme Inhibition Studies: Delving into the intricate world of enzyme regulation, Nα,Nω,Nω'-Tris-Z-L-arginine emerges as a potent inhibitor in investigations concerning nitric oxide synthase (NOS) enzymes. Scientists harness this compound to scrutinize the multifaceted regulatory mechanisms and functional intricacies of NOS within biochemical pathways. This exploration deepens our comprehension of nitric oxide's profound impact on cellular signaling and vascular functions.

Peptide Synthesis: Embarking on a journey into peptide synthesis, Nα,Nω,Nω'-Tris-Z-L-arginine assumes a crucial role in crafting arginine-containing peptides. By shielding the reactive amino groups with protective Z-groups, chemists achieve unparalleled precision in sequential peptide construction. This precision is imperative for synthesizing bioactive peptides crucial for therapeutic and diagnostic applications that propel the boundaries of biological research.

Cell Culture Studies: Unraveling the mysteries of cellular growth and function, Nα,Nω,Nω'-Tris-Z-L-arginine becomes a vital tool in modulating arginine's bioavailability—a pivotal amino acid in cell biology. Researchers leverage this compound to dissect the intricate processes of arginine transport and metabolism within cellular microenvironments. This research is fundamental to understanding the complex interplay of nutrient utilization and metabolic regulation across diverse cell types.

Pharmacokinetics and Drug Delivery: Embarking on a voyage through pharmacokinetics, Nα,Nω,Nω'-Tris-Z-L-arginine takes center stage in elucidating its influence on drug absorption and distribution dynamics. Frequently integrated into drug formulations aimed at enhancing therapeutic agent delivery and efficacy, this compound plays a pivotal role in optimizing drug administration strategies. Mastery of its pharmacokinetic profile catalyzes the development of more streamlined and effective drug delivery systems, revolutionizing the landscape of pharmaceutical research and development.

1. Structural basis of ligand binding modes at the neuropeptide Y Y1 receptor

Zhenlin Yang, et al. Nature. 2018 Apr;556(7702):520-524. doi: 10.1038/s41586-018-0046-x. Epub 2018 Apr 18.

Neuropeptide Y (NPY) receptors belong to the G-protein-coupled receptor superfamily and have important roles in food intake, anxiety and cancer biology 1,2 . The NPY-Y receptor system has emerged as one of the most complex networks with three peptide ligands (NPY, peptide YY and pancreatic polypeptide) binding to four receptors in most mammals, namely the Y1, Y2, Y4 and Y5 receptors, with different affinity and selectivity 3 . NPY is the most powerful stimulant of food intake and this effect is primarily mediated by the Y1 receptor (Y1R) 4 . A number of peptides and small-molecule compounds have been characterized as Y1R antagonists and have shown clinical potential in the treatment of obesity 4 , tumour 1 and bone loss 5 . However, their clinical usage has been hampered by low potency and selectivity, poor brain penetration ability or lack of oral bioavailability 6 . Here we report crystal structures of the human Y1R bound to the two selective antagonists UR-MK299 and BMS-193885 at 2.7 and 3.0 Å resolution, respectively. The structures combined with mutagenesis studies reveal the binding modes of Y1R to several structurally diverse antagonists and the determinants of ligand selectivity. The Y1R structure and molecular docking of the endogenous agonist NPY, together with nuclear magnetic resonance, photo-crosslinking and functional studies, provide insights into the binding behaviour of the agonist and for the first time, to our knowledge, determine the interaction of its N terminus with the receptor. These insights into Y1R can enable structure-based drug discovery that targets NPY receptors.

2. Biological properties of arginine-based gemini cationic surfactants

Lourdes Pérez, Maria Teresa García, Isabel Ribosa, Maria Pilar Vinardell, Angeles Manresa, Maria Rosa Infante Environ Toxicol Chem. 2002 Jun;21(6):1279-85.

Biological properties of novel gemini (double-chain/double-head) cationic surfactants, Nalpha,Nomega-bis(Nalpha-acylarginine)alpha,omega-alkylendiamides, so-called bis(Args), are reported. The effect of both the alkyl (10 and 12 carbon atoms) and the spacer chain (from 2-10 methylene groups) of bis(Args) on their antimicrobial activity, acute toxicity on Daphnia magna and Photobacterium phosphoreum, and aerobic biodegradability is studied. These surfactants constitute a novel class of chemicals of low toxicity with excellent surface properties and considerable antimicrobial activity. The aquatic toxicity of these compounds is lower than that of the conventional Monoquats. As regards the biodegradation test, the molecules with a spacer chain < or =6 methylene groups can be considered as ready biodegradable. The increase of hydrophobicity in the bis(Args) is a negative structural parameter for their environmental behavior.

3. Selective L-nitroargininylaminopyrrolidine and L-nitroargininylaminopiperidine neuronal nitric oxide synthase inhibitors

Jiwon Seo, Pavel Martásek, Linda J Roman, Richard B Silverman Bioorg Med Chem. 2007 Mar 1;15(5):1928-38. doi: 10.1016/j.bmc.2007.01.001. Epub 2007 Jan 4.

Selective inhibition of the localized excess production of NO by neuronal nitric oxide synthase (nNOS) has been targeted as a potential means of treating various neurological disorders. Based on observations from the X-ray crystal structures of complexes of nNOS with two nNOS-selective inhibitors, (4S)-N-{4-amino-5-[(2-amino)ethylamino]pentyl}-N'-nitroguanidine (L-Arg(NO2)-L-Dbu-NH2 (1) and 4-N-(Nomega-nitro-L-argininyl)-trans-4-amino-L-proline amide (2), a series of descarboxamide analogues was designed and synthesized (3-7). The most potent compound was aminopyrrolidine analogue 3, which exhibited better potency and selectivity for nNOS than parent compound 2. In addition, 3 provided higher lipophilicity and a lower molecular weight than 2, therefore having better physicochemical properties. Nalpha-Methylated analogues (8-11) also were prepared for increased lipophilicity of the inhibitors, but they had 4- to 5-fold weaker binding affinity compared to their parent compounds.