Nα-Z-L-arginine hydrochloride
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Nα-Z-L-arginine hydrochloride

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Category
CBZ-Amino Acids
Catalog number
BAT-003219
CAS number
56672-63-0
Molecular Formula
C14H20N4O4·HCl
Molecular Weight
344.80
Nα-Z-L-arginine hydrochloride
IUPAC Name
(2S)-5-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)pentanoic acid;hydrochloride
Synonyms
Z-L-Arg-OH HCl; (S)-2-(((Benzyloxy)carbonyl)amino)-5-guanidinopentanoic acid hydrochloride
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Density
1.33 g/cm3
Boiling Point
574°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C14H20N4O4.ClH/c15-13(16)17-8-4-7-11(12(19)20)18-14(21)22-9-10-5-2-1-3-6-10;/h1-3,5-6,11H,4,7-9H2,(H,18,21)(H,19,20)(H4,15,16,17);1H/t11-;/m0./s1
InChI Key
HHCPMSWPCALFQJ-MERQFXBCSA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)NC(CCCN=C(N)N)C(=O)O.Cl

Nα-Z-L-arginine hydrochloride is a biochemical reagent commonly used in peptide synthesis and other molecular biology applications. Here are some key applications of Nα-Z-L-arginine hydrochloride:

Peptide Synthesis: Nα-Z-L-arginine hydrochloride is frequently used as a protected amino acid in the synthesis of peptides. The Z (benzyloxycarbonyl) group serves as a protective group for the arginine side chain, preventing unwanted side reactions during peptide assembly. This makes it easier to achieve high-purity and correctly folded peptides for research and therapeutic use.

Enzyme Studies: In enzymology, Nα-Z-L-arginine hydrochloride is used as a substrate or inhibitor to study the activity and specificity of arginine-utilizing enzymes, such as arginases and nitric oxide synthases. By using this compound, researchers can gain insights into enzyme kinetics and mechanisms, which are critical for drug discovery and understanding metabolic pathways. This helps in the development of enzyme inhibitors or activators as potential therapeutic agents.

Protein Structure Analysis: Nα-Z-L-arginine hydrochloride can be employed in structural biology to facilitate the crystallization and structural determination of arginine-rich proteins. The presence of Nα-Z-L-arginine stabilizes the protein conformation and promotes crystal formation, enabling high-resolution X-ray crystallography studies. This is essential for elucidating the three-dimensional structures of proteins and understanding their functions.

Immunological Research: In immunology, Nα-Z-L-arginine hydrochloride is used in the synthesis of antigenic peptides for the study of immune responses. These peptides are employed in assays to investigate how T-cells recognize and respond to specific antigens, providing insights into immune mechanisms. This is valuable for vaccine development and understanding autoimmune diseases.

1.Co-delivery of peptide-modified cisplatin and doxorubicin via mucoadhesive nanocapsules for potential synergistic intravesical chemotherapy of non-muscle-invasive bladder cancer.
Lu S1, Xu L1, Kang ET1, Mahendran R2, Chiong E2, Neoh KG3. Eur J Pharm Sci. 2016 Mar 10;84:103-15. doi: 10.1016/j.ejps.2016.01.013. Epub 2016 Jan 15.
Synergistic effect against UMUC3 bladder cancer cells was demonstrated via a "two-in-one" combination of doxorubicin (Dox) and peptide-modified cisplatin (Pt-ALy) loaded in positively charged mucoadhesive chitosan-polymethacrylic acid (CM) nanocapsules. The in vitro killing efficacy of the dual drug-loaded nanocapsules (CM-Dox-PtALy) against UMUC3 cells after 4h- and 72h-treatment is much higher (with 5-16 times lower IC50) than either Dox- or Pt-ALy-loaded nanocapsules, resulting in combination indexes of much less than 1 (i.e. obvious synergism) at fractions of affected cells ranging from 0.2 to 0.8. The dose reduction index of Pt-ALy for 72h-treatment is higher than for 4h-treatment, suggesting that Dox in CM-Dox-PtALy played a more significant role in the synergy in the former. The drug-loaded CM nanocapsules are readily taken in by the cells as shown by flow cytometry, confocal laser scanning microscopy and inductively coupled plasma mass spectrometry.
2.Palladium-catalyzed enolate arylation as a key C-C bond-forming reaction for the synthesis of isoquinolines.
Pilgrim BS1, Gatland AE, Esteves CH, McTernan CT, Jones GR, Tatton MR, Procopiou PA, Donohoe TJ. Org Biomol Chem. 2016 Jan 21;14(3):1065-90. doi: 10.1039/c5ob02320c. Epub 2015 Dec 3.
The palladium-catalyzed coupling of an enolate with an ortho-functionalized aryl halide (an α-arylation) furnishes a protected 1,5-dicarbonyl moiety that can be cyclized to an isoquinoline with a source of ammonia. This fully regioselective synthetic route tolerates a wide range of substituents, including those that give rise to the traditionally difficult to access electron-deficient isoquinoline skeletons. These two synthetic operations can be combined to give a three-component, one-pot isoquinoline synthesis. Alternatively, cyclization of the intermediates with hydroxylamine hydrochloride engenders direct access to isoquinoline N-oxides; and cyclization with methylamine, gives isoquinolinium salts. Significant diversity is available in the substituents at the C4 position in four-component, one-pot couplings, by either trapping the in situ intermediate after α-arylation with carbon or heteroatom-based electrophiles, or by performing an α,α-heterodiarylation to install aryl groups at this position.
3.Molecular and biochemical evidence on the protective effects of embelin and carnosic acid in isoproterenol-induced acute myocardial injury in rats.
Kocak C1, Kocak FE2, Akcilar R3, Isiklar OO4, Kocak H2, Bayat Z5, Simsek H3, Taser F6, Altuntas I2. Life Sci. 2016 Feb 15;147:15-23. doi: 10.1016/j.lfs.2016.01.038. Epub 2016 Jan 25.
AIMS: Acute myocardial infarction is a serious acute cardiac disorder and heart disease is still a major public health problem in adults. We investigated the effects of embelin (EMB) and carnosic acid (CA) in animals with isoproterenol (ISO)-induced myocardial injury.
4.Protective effect of fasudil hydrochloride against acute renal injury in septicopyemia rats.
Tian XH1, Jiang WS2, Li XL1, Li MF1, Liu CL3, Li XX3. Asian Pac J Trop Med. 2015 Dec;8(12):1071-5. doi: 10.1016/j.apjtm.2015.11.008. Epub 2015 Nov 12.
OBJECTIVE: To observe the protective effect of fasudil hydrochloride against acute renal injury in septicopyemia rats.
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