CAS 1234-35-1

Benzyloxycarbonyl-L-arginine

Description:

Benzyloxycarbonyl-L-arginine, commonly referred to as Z-Arg, is a derivative of the amino acid arginine, characterized by the presence of a benzyloxycarbonyl (Z) protecting group. This compound is often utilized in peptide synthesis as a protective group for the amino group of arginine, facilitating the selective coupling of amino acids during the formation of peptides. The Z group enhances the stability of the amino acid during synthetic processes while allowing for subsequent deprotection under mild conditions. Benzyloxycarbonyl-L-arginine is typically a white to off-white crystalline solid, soluble in organic solvents such as dimethyl sulfoxide (DMSO) and methanol, but less soluble in water. Its molecular structure includes a guanidinium group, which contributes to its basicity and reactivity. The compound is significant in biochemical research and pharmaceutical applications, particularly in the development of peptide-based drugs and in studying protein interactions. Proper handling and storage are essential, as with many chemical substances, to maintain its integrity and effectiveness in laboratory settings.

Formula: C₁₄H₂₀N₄O₄

InChI: InChI=1S/C14H20N4O4/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)/t11-/m0/s1

InChI key: InChIKey=SJSSFUMSAFMFNM-NSHDSACASA-N

SMILES: C(OC(N[C@@H](CCCNC(=N)N)C(O)=O)=O)C1=CC=CC=C1

Synonyms:

• (2S)-2-[[(Benzyloxy)carbonyl]amino]-5-carbamimidamidopentanoic acid
• (2S)-5-(Diaminomethylideneazaniumyl)-2-(phenylmethoxycarbonylamino)pentanoate
• <span class="text-smallcaps">L</span>-Arginine, N²-[(phenylmethoxy)carbonyl]-
• <span class="text-smallcaps">L</span>-Arginine, N²-carboxy-, N-benzyl ester
• Arginine, N²-carboxy-, N-benzyl ester
• Arginine, N²-carboxy-, N²-benzyl ester, <span class="text-smallcaps">L</span>-
• Benzyloxycarbonyl-<span class="text-smallcaps">L</span>-arginine
• BenzyloxycarbonylLarginine
• Cbz-L-arginine
• N(alpha)-Benzyloxycarbonyl-L-arginine~Z-Arg-OH
• N(alpha)-Cbz-L-arginine
• N(alpha)-Z-L-arginine
• N-2-carbobenzyloxy-L-arginine
• N-Carbobenzoxyarginine
• N²-Benzyloxycarbonyl-<span class="text-smallcaps">L</span>-arginine
• N²-[(Phenylmethoxy)carbonyl]-<span class="text-smallcaps">L</span>-arginine
• N^α-(Benzyloxycarbonyl)arginine
• NALPHA-Benzyloxycarbonyl-L-arginine
• Na-Benzyloxycarbonyl-L-arginine
• Nalpha-CBZ-L-Arginine
• N~2~-[(benzyloxy)carbonyl]-N~5~-(diaminomethylidene)-L-ornithine
• Z-Arg
• Z-Arg-OH
• Z-L-Arg-OH
• na-cbz-L-arginine free acid
• N2-[(Phenylmethoxy)carbonyl]-L-arginine
• Arginine, N2-carboxy-, N2-benzyl ester, L-
• L-Arginine, N2-carboxy-, N-benzyl ester
• Arginine, N2-carboxy-, N-benzyl ester

L-Arginine, N2-[(phenylmethoxy)carbonyl]-

CAS: 1234-35-1

Formula: C₁₄H₂₀N₄O₄

Purity: 98%

Color and Shape: Solid

Molecular weight: 308.3330

Ref: IN-DA000KIQ

Nα-Cbz-L-Arginine

CAS: 1234-35-1

Nα-Cbz-L-Arginine

Purity: 97%

Molecular weight: 308.33g/mol

Ref: 54-OR1014244

Z-Arg-OH

CAS: 1234-35-1

Formula: C₁₄H₂₀N₄O₄

Purity: ≥ 98.0%

Color and Shape: White powder

Molecular weight: 308.34

Ref: 7W-GM5373

Nα-Carbobenzoxy-L-arginine

CAS: 1234-35-1

Formula: C₁₄H₂₀N₄O₄

Purity: >97.0%(T)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 308.34

Ref: 3B-C0757

Z-L-Arg-OH

CAS: 1234-35-1

Z-L-Arg-OH is a peptide hormone that belongs to the group of peptide hormones. It has been shown to have a stabilizing effect on hydrolysis reactions and its ph optimum is between 6.0 and 7.5. Amino acid analysis has shown that this molecule contains two amino acids, L-arginine as the first amino acid and L-arginine as the last amino acid. The trifluoroacetic acid (TFA) catalyses the hydrolysis reaction at a rate that is much faster than other acids such as phosphoric acid or nitric acid. Kinetic studies have been done using soybean trypsin enzyme preparations and Z-L-Arg-OH shows an increase in activity with higher concentrations of trypsin. Enzyme preparations show an increase in activity for Z-L-Arg-OH when it is mixed with another enzyme such as pepsin or papain. Acid analysis also showed that Z-

Formula: C₁₄H₂₀N₄O₄

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 308.34 g/mol

Ref: 3D-FA33481

Z-Arg-OH

CAS: 1234-35-1

M03028 - Z-Arg-OH

Formula: C₁₄H₂₀N₄O₄

Purity: 98%

Color and Shape: Solid, No data available.

Molecular weight: 308.338

Ref: 10-M03028

Z-L-Arginine extrapure, 99%

CAS: 1234-35-1

Formula: C₁₄H₂₀N₄O₄

Purity: min. 99%

Color and Shape: White to off-white, Crystalline powder

Molecular weight: 308.3

Ref: SR-60020

Z-L-Arginine

Controlled Product

CAS: 1234-35-1

Applications Z-L-Arginine is used in the synthesis of renin inhibitors containing phosphorous acid derivatives at the scissile bond. Also used in the synthesis of a peptide deformylase inhibitor BB-3497.
References Allen, M. et al.: J. Med. Chem., 32, 1652 (1989); Davies, S. et al.: Bioorg. Med. Chem. Lett., 13, 2715 (2003);

Formula: C₁₄H₂₀N₄O₄

Color and Shape: Neat

Molecular weight: 308.33

Ref: TR-A769400