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Application Area

Z-Arg(NO2)-OH

* 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-006070

CAS number

2034-98-5

Molecular Formula

C14H19N5O6

Molecular Weight

353.3

IUPAC Name

(2S)-5-[[amino(nitramido)methylidene]amino]-2-(phenylmethoxycarbonylamino)pentanoic acid

Synonyms

N-α-Carbobenzyloxy-Ng-nitro-L-arginine

InChI

InChI=1S/C14H19N5O6/c15-13(18-19(23)24)16-8-4-7-11(12(20)21)17-14(22)25-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,17,22)(H,20,21)(H3,15,16,18)/t11-/m0/s1

InChI Key

BZPCSFNCKORLQG-NSHDSACASA-N

Canonical SMILES

C1=CC=C(C=C1)COC(=O)NC(CCCN=C(N)N[N+](=O)[O-])C(=O)O

Z-Arg(NO2)-OH, also known as nitroarginine, serves as a potent nitric oxide synthase inhibitor with diverse applications in scientific research. Here are the key applications of Z-Arg(NO2)-OH, presented with high perplexity and burstiness:

Cardiovascular Research: At the forefront of cardiovascular investigations, Z-Arg(NO2)-OH is harnessed to delve into the intricate role of nitric oxide in blood vessel functionality and the regulation of blood pressure. By impeding nitric oxide synthesis, researchers can unravel the repercussions on vasoconstriction and hypertension, shedding light on the pathophysiological complexities underpinning cardiovascular ailments and paving the way for novel therapeutic avenues.

Neurobiological Studies: Delving into the realms of neuroscience, Z-Arg(NO2)-OH is a pivotal tool in deciphering the functional significance of nitric oxide within the intricate landscapes of the nervous system. Nitric oxide, serving as a neurotransmitter, plays pivotal roles in processes such as synaptic plasticity and neurotoxicity. By curtailing its production, scientists can dissect its profound influence on neural signaling mechanisms and the pathogenesis of neurodegenerative maladies like Alzheimer's disease, enriching our understanding of brain function.

Immunological Research: In the realm of immunology, Z-Arg(NO2)-OH emerges as a cornerstone for unraveling the multifaceted roles of nitric oxide in orchestrating immune responses. Nitric oxide proves crucial in pathogen defense and inflammation regulation. By inhibiting its production, researchers can delineate its impact on immune cell dynamics and the development of inflammatory disorders, paving the way for novel insights into immune-mediated diseases.

Cancer Research: In the domain of oncological inquiries, Z-Arg(NO2)-OH plays a pivotal role in unraveling the intricate involvement of nitric oxide in tumor progression and metastasis. Nitric oxide's role in promoting angiogenesis and sustaining cancer cell survival makes it a prime target for therapeutic interventions. By inhibiting nitric oxide production, researchers can unveil novel strategies for targeting nitric oxide pathways in cancer treatment, offering promising avenues for combating malignancies.

1. Synthesis of arginine aldehydes for the preparation of pseudopeptides

G Guichard, J P Briand, M Friede Pept Res. 1993 May-Jun;6(3):121-4.

The synthesis of optically active aldehydes from N alpha-Boc-amino acids by reduction of the corresponding O,N-dimethyl-hydroxamates, while proceeding smoothly for most amino acids, has presented significant problems in the case of arginine. We demonstrate here that this difficulty can be overcome by the use of arginine derivatives in which the guanidino group is completely protected, such as in the case of N alpha-Boc-Arg(di-Z). In the case of nitro-, tosyl- or pmc-protected arginine, no satisfactory aldehyde formation can be obtained. It appears that in these cases the guanidino group is insufficiently protected and inhibits the formation of aldehydes. We also demonstrate that aldehydes can be readily obtained from N alpha-Fmoc protected amino acids.

2. New tris-alkoxycarbonyl arginine derivatives for peptide synthesis

Jan Izdebski, Tomasz Gers, Danuta Kunce, Paweł Markowski J Pept Sci. 2005 Jan;11(1):60-4. doi: 10.1002/psc.585.

alpha-Alkoxycarbonyl protected ornithines were treated with N,N'-[Z(2Cl)](2)-S-methylisothiourea and N,N'-[Z(2Br)](2)-S-methylisothiourea, N,N'-Z(2)-S-methylisothiourea and N,N'-Boc(2)-S-methylisothiourea to form N(alpha, omega, omega')-tris-alkoxycarbonyl arginines. Two of them, Boc-Arg-{omega,omega'-[Z(2Br)](2)}-OH and Boc-Arg-{omega,omega'-[Z(2Cl)](2)}-OH, were used for the synthesis of dermorphin fragments containing two or three arginine residues. Examination of the products by HPLC and ESI-MS revealed that the purity of the materials obtained with the use of the new derivatives was higher than that obtained in concurrent syntheses in which Boc-Arg(Tos) was used.

3. Synthesis of N alpha-protected aminoacyl 7-amino-4-methyl-coumarin amide by phosphorous oxychloride and preparation of specific fluorogenic substrates for papain

L C Alves, P C Almeida, L Franzoni, L Juliano, M A Juliano Pept Res. 1996 Mar-Apr;9(2):92-6.

We report an improved procedure for the synthesis of fully protected aminoacyl 7-amino-4-methylcoumarin amide (MCA) employing the phosphorous oxychloride anhydride method. Seven Boc-X-MCA [where X = Arg(NG Tos), Cys(S-Bzl), Thr(O-Bzl), Ser(O-Bzl), Phe, Leu and Gly] and Z-Tyr(O-Me) were synthesized using this procedure, with yields ranging from 50% to 75%. These aminoacyl-MCA derivatives were employed for the synthesis of epsilon-NH2-caproyl-Leu-X-MCA, a fluorescent peptide series, which were assayed as papain substrates. All of them were completely hydrolyzed by papain, indicating that all of the Boc-X-MCA derivatives obtained were practically free of racemization. Since epsilon-NH2-Caproyl-Leu-(S-Bzl)Cys-MCA is very susceptible to hydrolysis by papain, quite resistant to hydrolysis by chymotrypsin and not hydrolyzed by trypsin, it is recommended for assays of thiol-proteinases in which specificity is required.