Nα-Z-L-arginine benzyl ester
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Nα-Z-L-arginine benzyl ester

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Category
CBZ-Amino Acids
Catalog number
BAT-000460
CAS number
103305-87-9
Molecular Formula
C21H26N4O4·C7H8O3S
Molecular Weight
570.66
IUPAC Name
benzyl (2S)-5-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)pentanoate
Synonyms
Z-Arg-OBzl TosH; Benzyl (2S)-5-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)pentanoate
Appearance
White powder
Purity
≥ 98% (HPLC)
Storage
Store at 2-8 °C
InChI
InChI=1S/C21H26N4O4/c22-20(23)24-13-7-12-18(19(26)28-14-16-8-3-1-4-9-16)25-21(27)29-15-17-10-5-2-6-11-17/h1-6,8-11,18H,7,12-15H2,(H,25,27)(H4,22,23,24)/t18-/m0/s1
InChI Key
CJKBMTWHZUGZIL-SFHVURJKSA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)C(CCCN=C(N)N)NC(=O)OCC2=CC=CC=C2

Nα-Z-L-Arginine benzyl ester, a derivative of the essential amino acid L-arginine, finds several critical applications in biochemical and pharmaceutical research. One of its key uses is as a reagent in peptide synthesis. Peptide synthesis is vital for creating peptide-based drugs and studying protein functions, and Nα-Z-L-Arginine benzyl ester plays an essential role due to its protected arginine group, facilitating the construction of peptide chains without unwanted reactions. In this capacity, it ensures the accurate assembly of sequences which are crucial for therapeutic peptides.

Another significant application of Nα-Z-L-Arginine benzyl ester lies in its role as a substrate and intermediate in enzymatic studies. Researchers utilize this compound to investigate the activity of enzymes that metabolize arginine. For example, it serves as a model substrate to study arginase and nitric oxide synthase (NOS), enzymes involved in the urea cycle and nitric oxide production. By providing insights into these enzymatic processes, Nα-Z-L-Arginine benzyl ester helps to develop treatments for diseases associated with nitric oxide dysregulation, such as cardiovascular disorders.

Nα-Z-L-Arginine benzyl ester is also employed as a precursor in the synthesis of more complex bioactive compounds. This involves its use in generating compounds with potential medicinal properties, including inhibitors for specific enzymes or pathways. Since arginine and its derivatives play a pivotal role in cellular functions, researchers harness this compound to create novel pharmacological agents that might ameliorate conditions like hypertension, cancer, and immune-related diseases. Its benzyl ester group provides stability and control during chemical reactions, enhancing the reliability of synthetic routes.

Lastly, Nα-Z-L-Arginine benzyl ester is useful in the formulation of diagnostic assays. In medical diagnostics, the accurate measurement of enzyme activity or the presence of specific metabolites can be critical. This compound can be incorporated into assay kits to examine arginase activity or nitric oxide synthase dynamics in biological samples. By offering a reliable, consistent standard, it helps ensure that diagnostics are precise, leading to better disease monitoring and management. Hence, Nα-Z-L-Arginine benzyl ester not only supports basic research but also has direct implications in clinical diagnostics.

2. Electrochemical Benzylic C(sp3)-H Acyloxylation
Alexander P Atkins, Albert C Rowett, David M Heard, Joseph A Tate, Alastair J J Lennox Org Lett. 2022 Jul 22;24(28):5105-5108. doi: 10.1021/acs.orglett.2c01930. Epub 2022 Jul 13.
The development of sustainable C(sp3)-H functionalization methods is of great interest to the pharmaceutical and agrochemical industries. Anodic oxidation is an efficient means of producing benzylic cations that can undergo subsequent in situ nucleophilic attack to afford functionalized benzylic products. Herein, we demonstrate the suitability of carboxylic acids as nucleophiles to yield benzylic esters. This method employs a series of secondary benzylic substrates and functionalized carboxylic acids and is demonstrated on a gram scale in flow.
3. N-carboxy-L-aspartic anhydride benzyl ester
Hitoshi Kanazawa, Jun Magoshi Acta Crystallogr C. 2003 Mar;59(Pt 3):o159-61. doi: 10.1107/s0108270103002567. Epub 2003 Feb 28.
The structure of the title compound, benzyl (1,2,3,4-tetrahydro-2,5-dioxo-1,3-oxazol-4-yl)acetate, C(12)H(11)NO(5), has been determined in an attempt to explain the polymerization observed in the solid state. The molecules are linked by intermolecular hydrogen bonds between the imino group of the five-membered ring and an adjacent carbonyl O atom, along the c axis. Intramolecular hydrogen bonds are also formed, between the imino group and the carbonyl O atom of the ester group. The five-membered rings are arranged in a layer, sandwiched by layers incorporating the benzyl groups. This structure is thought to be preferable for the polymerization of the compound in the solid state, because the five-membered rings can react with each other in the layer.
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