1234-35-1

Basic information

• Product Name: Nalpha-Cbz-L-Arginine
• Synonyms: n2-[(phenylmethoxy)carbonyl]-l-arginin;Nα-Z-L-Arginine;N2-Carbobenzyloxy-L-arginine ;BenzyloxycarbonylLarginine;N(alpha)-Benzyloxycarbonyl-L-arginine~Z-Arg-OH;Na-Benzyloxycarbonyl-L-arginine;na-cbz-L-arginine free acid;N2-[(phenylmethoxy)carbonyl]-L-arginine
• CAS NO: 1234-35-1
• Molecular Formula: C₁₄H₂₀N₄O₄
• Molecular Weight: 308.33
• EINECS: 214-973-6
• Product Categories: PROTECTED AMINO ACID & PEPTIDES;Arginine [Arg, R];Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Z-Amino acid series
• Mol File: 1234-35-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 171-174 °C (dec.)(lit.)
• Boiling Point: 448.73°C (rough estimate)
• Appearance: White to off white powder
• Density: 1.1765 (rough estimate)
• Refractive Index: -10 ° (C=5.5, 0.2mol/L HCl)
• Storage Temp.: 2-8°C
• Solubility: DMSO, Water
• PKA: 3.90±0.21(Predicted)
• BRN: 2169267
• CAS DataBase Reference: Nalpha-Cbz-L-Arginine(CAS DataBase Reference)
• NIST Chemistry Reference: Nalpha-Cbz-L-Arginine(1234-35-1)
• EPA Substance Registry System: Nalpha-Cbz-L-Arginine(1234-35-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26-S24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1234-35-1(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

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.

InChI:InChI=1/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

Upstream product

• 68172-31-6 α-carbobenzoxy-L-arginine p-nitrophenyl ester 
• 100-51-6 benzyl alcohol 
• 2304-98-5 N₅-[imino(nitroamino)methyl]-N₂-[(phenylmethoxy)carbonyl]-L-ornithine 
• 420-04-2 CYANAMID 
• 2640-58-6 Nα-benzyloxycarbonyl-L-ornithine 
• 5241-58-7 L-Phenylalanine amide 
• 501-53-1 benzyl chloroformate 
• 19503-22-1 1H-benzotriazole-1-carboxamidine hydrochloride 
• 29542-03-8 Z-Arg-pNA 
• 74-79-3 L-arginine 

Downstream Products

• 75813-41-1 N^α-benzyloxycarbonyl-N^G-(4-methoxy-2,6-dimethylbenzenesulphonyl)arginine 
• 116115-28-7 N^α-Benzyloxycarbonyl-N^ω-(9-anthracenesulfonyl)-L-arginine 
• 80745-06-8 Z-Arg(Mtb)-OH 
• 82774-92-3 Z-L-Arg(H*HCl)-L-Trp-OMe 
• 73496-38-5 7-(N^α-Z-L-Argininamido)-4-(trifluoromethyl)-coumarin Hydrochloride 
• 112160-32-4 N_α-benzyloxycarbonyl-N_G-(2,2,5,7,8-pentamethylchroman-6-sulphonyl)-L-arginine 
• 80745-08-0 Z-Arg(Mtr)-OH 
• 126811-00-5 Z-Arg-Gln-Gln-Gly-OBzl(4NO₂) 
• 93287-51-5 (S)-2-[(S)-2-({(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-5-guanidino-pentanoylamino)-5-guanidino-pentanoyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionylamino]-3-(1H-imidazol-4-yl)-propionic acid methyl ester 
• 74-79-3 L-arginine 
• 100-51-6 benzyl alcohol 
• 136315-46-3 N^α-Benzyloxycarbonyl-L-leucyl-L-arginyl-L-prolylglycine amide acetate sesquihydrate 
• 74-79-3 L-arginine 
• 23257-94-5 N^α-Carbobenzoxy-L-argininethylester 

Relevant articles and documents

NaBH4 - A novel method for the deprotection of Nω-nitro-arginine

The selective deprotection of Nω-nitro-arginine derivatives represents a major preparative challenge. This problem can be circumvented by the use of catalytic hydrogenation, but often high pressure, elevated temperature, and/or long reaction times are needed. In certain cases hydrogenation is not suitable, for example, small-scale reactions, parallel synthesis, or due to selectivity issues. Herein, we demonstrate for the first time, the use of NaBH4 in the presence of a metal ion catalyst for the removal of the Nω-nitro moiety under simple, 'open-vessel' conditions. This process using NaBH4 does not remove the benzyloxycarbonyl-protecting group; thus the method is orthogonal for this protecting scheme.

Direct guanylation of amino groups by cyanamide in water: Catalytic generation and activation of unsubstituted carbodiimide by scandium(iii) triflate

Guanylation proceeded efficiently upon treatment of the various amines with cyanamide in the presence of catalytic amounts of scandium(III) triflate under mild conditions. The method did not require the guanylation reagents to be preactivated, and the reaction proceeded efficiently in water. The method, therefore, has practical utility for substrates that dissolve only in aqueous solutions, for example, peptides or pharmacologically important compounds. Georg Thieme Verlag Stuttgart New York.

The total large-scale synthesis of argiopine

The total large-scale synthesis of a natural toxin argiopine, a polymethylenepolyamine derivative, was developed. It consisted of 26 stages and included three key block schemes. Most of the stages proceeded quantitatively, which excluded the necessity of using the chromatographic separation of intermediates.