Nα-Z-Nω-(4-toluenesulfonyl)-L-arginine
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Nα-Z-Nω-(4-toluenesulfonyl)-L-arginine

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Category
CBZ-Amino Acids
Catalog number
BAT-003256
CAS number
13650-38-9
Molecular Formula
C21H26N4O6S
Molecular Weight
462.50
Nα-Z-Nω-(4-toluenesulfonyl)-L-arginine
IUPAC Name
(2S)-5-[[amino-[(4-methylphenyl)sulfonylamino]methylidene]amino]-2-(phenylmethoxycarbonylamino)pentanoic acid
Synonyms
Z-L-Arg(Tos)-OH; N-Alpha-Carbobenzoxy-N-Omega-P-Toluenesulfonyl L-Arginine
Appearance
White powder
Purity
≥ 99% (TLC)
Melting Point
71-83 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C21H26N4O6S/c1-15-9-11-17(12-10-15)32(29,30)25-20(22)23-13-5-8-18(19(26)27)24-21(28)31-14-16-6-3-2-4-7-16/h2-4,6-7,9-12,18H,5,8,13-14H2,1H3,(H,24,28)(H,26,27)(H3,22,23,25)/t18-/m0/s1
InChI Key
BHQRCFPZYISVMF-SFHVURJKSA-N
Canonical SMILES
CC1=CC=C(C=C1)S(=O)(=O)NC(=NCCCC(C(=O)O)NC(=O)OCC2=CC=CC=C2)N

Nα-Z-Nω-(4-toluenesulfonyl)-L-arginine, a specialized chemical compound crucial in peptide synthesis and biochemical research, finds diverse applications with high perplexity and burstiness.

Peptide Synthesis: Serving as a shielded arginine derivative, Nα-Z-Nω-(4-toluenesulfonyl)-L-arginine plays a pivotal role in peptide synthesis. Its protective groups act as sentinels, warding off unwanted side reactions during peptide bond formation, ensuring the meticulous assembly of intricate peptides for scientific investigation and therapeutic exploration.

Enzyme Inhibition Studies: Delving into the realm of enzyme inhibition, this compound emerges as a key player in the study of arginase and nitric oxide synthase inhibition. By integrating Nα-Z-Nω-(4-toluenesulfonyl)-L-arginine into enzyme assays, researchers unlock the complexities of inhibitory effects and enzyme kinetics. This application sheds light on enzyme regulation, paving the way for potential therapeutic inhibitors to emerge.

Proteomics Research: In the domain of proteomics, Nα-Z-Nω-(4-toluenesulfonyl)-L-arginine unveils its utility in labeling and modifying proteins for mass spectrometry analysis. By utilizing this compound, researchers enhance the detectability of proteins, enabling precise identification and quantification in studies encompassing protein expression, post-translational modifications, and protein-protein interactions.

Drug Development: Positioned at the forefront of drug development, Nα-Z-Nω-(4-toluenesulfonyl)-L-arginine propels the creation of small-molecule inhibitors targeting arginine-utilizing enzymes. Through the strategic use of this compound, scientists engineer and evaluate inhibitors with therapeutic potential in diseases where these enzymes hold sway. This application accelerates the discovery of potent drug candidates and fine-tunes their effectiveness, heralding advancements in therapeutic interventions.

1. A comparison of EDHF-mediated and anandamide-induced relaxations in the rat isolated mesenteric artery
R White, C R Hiley Br J Pharmacol. 1997 Dec;122(8):1573-84. doi: 10.1038/sj.bjp.0701546.
1. Relaxation of the methoxamine-precontracted rat small mesenteric artery by endothelium-derived hyperpolarizing factor (EDHF) was compared with relaxation to the cannabinoid, anandamide (arachidonylethanolamide). EDHF was produced in a concentration- and endothelium-dependent fashion in the presence of NG-nitro-L-arginine methyl ester (L-NAME, 100 microM) by either carbachol (pEC50 [negative logarithm of the EC50] = 6.19 +/- 0.01, Rmax [maximum response] = 93.2 +/- 0.4%; n = 14) or calcium ionophore A23187 (pEC50 = 6.46 +/- 0.02, Rmax = 83.6 +/- 3.6%; n = 8). Anandamide responses were independent of the presence of endothelium or L-NAME (control with endothelium: pEC50 = 6.31 +/- 0.06, Rmax = 94.7 +/- 4.6%; n = 10; with L-NAME: pEC50 = 6.33 +/- 0.04, Rmax = 93.4 +/- 6.0%; n = 4). 2. The selective cannabinoid receptor antagonist, SR 141716A (1 microM) caused rightward shifts of the concentration-response curves to both carbachol (2.5 fold) and A23187 (3.3 fold). It also antagonized anandamide relaxations in the presence or absence of endothelium giving a 2 fold shift in each case. SR 141716A (10 microM) greatly reduced the Rmax values for EDHF-mediated relaxations to carbachol (control, 93.2 +/- 0.4%; SR 141716A, 10.7 +/- 2.5%; n = 5; P < 0.001) and A23187 (control, 84.8 +/- 2.1%; SR 141716A, 3.5 +/- 2.3%; n = 6; P < 0.001) but caused a 10 fold parallel shift in the concentration-relaxation curve for anandamide without affecting Rmax.
2. Synthesis of 2-methyl and 2-carboxymethyl derivatives of ornithine and arginine
C G Unson, B W Erickson Int J Pept Protein Res. 1983 Jul;22(1):50-6. doi: 10.1111/j.1399-3011.1983.tb02067.x.
Synthesis and characterization of a dozen derivatives of ornithine and arginine bearing 2-methyl or 2-carboxymethyl substituents are described. These substituents were introduced by dilithiation of 3-(4-methoxybenzylidineamino)-2-piperidinone with lithium diisopropylamide followed by regiospecific alkylation at C-3 with iodomethane or ethyl bromoacetate. 2-Methyl-D,L-ornithine was obtained in three steps from 3-amino-2-piperidinone in 68% overall yield, and 2-carboxymethyl-D,L-ornithine was isolated in 56% overall yield. 2-Methyl- and 2-carboxymethyl-D,L-arginine were obtained by mild acid hydrolysis to remove the 4-methoxybenzylidine group, N-acylation with 4-toluenesulfonyl chloride, mild alkaline hydrolysis of the lactam ring and the ester group, guanidination of the 5-amino group with O-methylisourea, and strong acid hydrolysis to remove the 4-tolunenesulfonyl group. Several of these compounds are inhibitors of carboxypeptidase B.
3. Trehalose-functional glycopeptide enhances glycerol-free cryopreservation of red blood cells
Bo Liu, Qifa Zhang, Yunhui Zhao, Lixia Ren, Xiaoyan Yuan J Mater Chem B. 2019 Sep 25;7(37):5695-5703. doi: 10.1039/c9tb01089k.
The long-term cryopreservation of cells, tissues and organs is limited by both osmotic stress and ice injury during freezing or thawing. Introduction of biocompatible cryoprotective agents is promising for cell cryopreservation based on membrane stabilization of glycopeptides and trehalose. Herein, a series of trehalose-functional (glyco)peptides were synthesized by successively tethering Nω-(4-toluenesulfonyl)-l-arginine and carboxylated trehalose to the side amino groups of ε-polylysine. The specifically synthesized glycopeptide demonstrated enhanced cryosurvival of sheep red blood cells (RBCs) from 49.1 ± 0.9% to 75.0 ± 2.4% at pH 7.4, along with trehalose molecules. Cryopreservation via membrane stabilization was proposed such that the glycopeptide could attach on the cell membrane surface of RBCs to protect the cell membrane from osmotic injury by electrostatic interactions, π-π stacking and hydrogen bonding. Meanwhile, trehalose could prevent RBCs from ice injury via ice recrystallization inhibition activity. Thus, membrane protection for preventing osmotic stress and ice injury could be boosted via synergistic interaction between the glycopeptide and trehalose. The combined usage of biocompatible glycopeptides and trehalose could potentially be applied in the glycerol-free cryopreservation of cells and tissues in biomedicine.
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