6366-70-7

Basic information

• Product Name: N6-Cbz-L-Lysine benzyl ester hydrochloride
• Synonyms: N-Benzyloxycarbonyl-L-lysine benzyl ester hydrochloride;Lys(Z)-OBzl·HCl;N-ε-Z-L-lysine benzyl ester hydrochloride;N-EPSILON-CBZ-L-LYSINE BENZYL ESTERHYDRO CHLORIDE C;H-LYS(Z)-OBZL.HCL 99+%;H-Lys(Cbz)-OBzl·Hydrochloride;L-LYS(Z)-OBZL.HCL;Nε-Cbz-L-Lysine benzyl ester hydrochloride
• CAS NO: 6366-70-7
• Molecular Formula: C₂₁H₂₆N₂O₄*ClH
• Molecular Weight: 406.9
• EINECS: 228-859-9
• Product Categories: Amino Acid Derivatives;Amino Acids;Lysine [Lys, K];Amino Acids and Derivatives;Amino hydrochloride;Amino Acids & Derivatives;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 6366-70-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 138-140 °C
• Boiling Point: 536.6 °C at 760 mmHg
• Flash Point: 278.3 °C
• Appearance: White to off-white/Powder
• Density: 1.163g/cm3
• Vapor Pressure: 1.37E-11mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: Store at RT.
• Solubility: DMSO, DMF, Methanol
• BRN: 3580519
• CAS DataBase Reference: N6-Cbz-L-Lysine benzyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N6-Cbz-L-Lysine benzyl ester hydrochloride(6366-70-7)
• EPA Substance Registry System: N6-Cbz-L-Lysine benzyl ester hydrochloride(6366-70-7)

Safety Data

• WGK Germany: 3
• RTECS: OL5685000
• Hazardous Substances Data: 6366-70-7(Hazardous Substances Data)

Usage

Description

N6-Cbz-L-Lysine benzyl ester hydrochloride is a chemical compound that serves as a building block in the synthesis of peptides and proteins. It is a protected form of L-lysine, an essential amino acid, with a carbobenzyloxy (Cbz) group attached to the amino group and a benzyl ester group attached to the carboxyl group. The hydrochloride form indicates that it is a salt derived from the reaction of the compound with hydrochloric acid. This modification enhances the stability and solubility of the compound, making it suitable for various applications in the pharmaceutical and biotechnology industries.

Uses

Used in Pharmaceutical Industry:
N6-Cbz-L-Lysine benzyl ester hydrochloride is used as a synthetic intermediate for the preparation of pseudopeptides as thrombolytic agents. These agents are designed to dissolve blood clots, which can be crucial in the treatment of conditions such as stroke, deep vein thrombosis, and pulmonary embolism. N6-Cbz-L-Lysine benzyl ester hydrochloride's protected structure allows for the controlled synthesis of complex peptide sequences, which can be further modified to enhance their therapeutic properties.
In the field of peptide synthesis, N6-Cbz-L-Lysine benzyl ester hydrochloride is used as a protected amino acid for the stepwise assembly of peptides. The Cbz group protects the amino group from unwanted side reactions during the synthesis process, while the benzyl ester group shields the carboxyl group. This protection allows chemists to selectively deprotect and couple amino acids in a controlled manner, ultimately leading to the formation of the desired peptide sequence.
Additionally, N6-Cbz-L-Lysine benzyl ester hydrochloride can be used in the development of novel drug delivery systems. N6-Cbz-L-Lysine benzyl ester hydrochloride's unique structure and properties can be exploited to design targeted drug carriers, which can improve the bioavailability and therapeutic efficacy of peptide-based drugs. This can be particularly useful in the treatment of various diseases, including cancer, where peptide-based therapeutics have shown promise.

InChI:InChI=1/C21H26N2O4/c22-19(20(24)26-15-17-9-3-1-4-10-17)13-7-8-14-23-21(25)27-16-18-11-5-2-6-12-18/h1-6,9-12,19H,7-8,13-16,22H2,(H,23,25)

Upstream product

• 77236-13-6 N-α-tert-Butyloxycarbonyl-N-ε-carbobenzoxy-L-lysine benzyl ester 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 1155-64-2 N₆-[(benzyloxy)carbonyl]-L-lysine 
• 100-51-6 benzyl alcohol 
• 2389-45-9 Boc-Lys(Z)-OH 

Downstream Products

• 114856-02-9 Boc-Ala-Lys(Z)-OBzl 
• 233258-52-1 Boc-S-β-HAla-Lys(Z)-OBn 
• 233258-47-4 Boc-S-β-HAla-R-HB-Lys(Z)-OBn 
• 1063606-34-7 N^α-[5-(benzyloxycarbonylamino)pentylcarbonyl]-N^ε-(benzyloxycarbonyl)-L-lysine benzyl ester 
• 166267-89-6 Boc-Asp(OBzl)-Cys(Acm)-Lys(Z)-OBzl 
• 166267-90-9 Boc-Glu(OBzl)-Asp(OBzl)-Cys(Acm)-Lys(Z)-OBzl 
• 943443-89-8 N^ω-benzyloxycarbonyl-N^α-[4-(1',3'-dioxyl-4',4',5',5'-tetramethyldihydroimidazol-2'-yl)phenyloxyacetyl]-L-lysine benzyl ether 
• 1034535-40-4 N-(3S-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-L-lysine(Z) benzyl ester 
• 37941-56-3 Boc-Gly-Lys(Z)-OBzl 
• 1260170-23-7 Nα-((3-benzyloxycarbonyl-β-carbolin-1-yl)ethyl)-Nω-(benzyloxycarbonyl)-L-lysine benzyl ester 

Relevant articles and documents

Synthesis of the Tripeptides Tyr-Thr-Lys Phosphorylated with Isopropyl Methyl- and (Deuteromethyl)phosphonochloridates as Reference Standards for the Analysis of Biomedical Samples

A procedure for the phosphorylation of the tripeptide Tyr-Thr-Lys with isopropyl methyl- or (deuteromethyl)phosphonochloridate is developed. The phosphorylated tripeptides are intended for use as reference standards in the analysis of blood samples of people suspected to have been exposed to acetylcholinesterase inhibitors. Conditions of hromatographic separation and purification of the synthesized compounds are determined and optimized, which ensures the preparation of high-purity phosphorylated tripeptides.

A class of novel carboline intercalators: Their synthesis, in vitro anti-proliferation, in vivo anti-tumor action, and 3D QSAR analysis

Based on DOCK scores 18 N-(3-benzyloxycarbonylcarboline-1-yl)ethylamino acid benzylesters (6a-r) were synthesized as anti-tumor agents. Their IC 50 values against five human carcinoma cell lines ranged from 11.1 μM to more than 100 μM. The in vivo assay identified five derivatives of them had no anti-tumor action, the anti-tumor activity of nine derivatives of them equaled that of cytarabine, and the anti-tumor activity of three derivatives of them was higher than that of cytarabine. The UV and fluorescence spectra, as well as the relative viscosity and melting temperature measurements of calf thymus DNA (CT DNA) with and without the representative compound suggested that DNA intercalation could be their action mechanism. The 3D QSAR analysis of N-(3-benzyloxycarbonylcarboline-1-yl)ethylamino acid benzylesters (6a-r) revealed that their in vivo anti-tumor activity significantly depends on the molecular electrostatic and steric fields of the side chain of the amino acid residue.

Granulopoiesis Inhibiting Factor: Synthesis and Biological Activity

Three schemes of synthesis for pentapeptide Glp-Glu-Asp-Cys-Lys-OH were compared.Acetamidomethyl protection was used for the mercapto group of cysteine.For the same purpose, cystine was used as the starting compound for synthesis.The optimal method was shown to be the solid phase method with S-acetamidomethyl cysteine protection that can be removed by mercuric acetate before the cleavage of a peptide from a polymer.The stabilized peptide inhibits proliferation of bone marrow cells of patients with chronic myeloleukemia 5- to 20-fold and has a less pronounced effect (up to 2-fold inhibition) on peripheral blood cells.Thus, its application for the therapy of hemoblastoses is promising. Key words: granulopoiesis inhibiting factor, solid phase peptide synthesis, cysteine-containing pentapeptide