6327-59-9

Basic information

• Product Name: H-ASP(OBZL)-OBZL HCL
• Synonyms: L-ASPARTIC ACID DIBENZYL ESTER HYDROCHLORIDE;L-ASPARTIC ACID-ALPHA, BETA-DIBENZYL ESTER HYDROCHLORIDE;L-ASPARTIC ACID ALPHA,BETA-DIBENZYL ESTER HYDROCHLORIDE SALT;H-ASP(OBZL)-OBZL HCL;H-L-Asp(Bzl)-OBzl*HCl;L-Aspartic acid 1,4-bis-benzyl ester hydrochloride;H-Asp(OBzl)-OBzlCl;L-Aspartic acid, bis(phenylMethyl) ester, hydrochloride
• CAS NO: 6327-59-9
• Molecular Formula: C₁₈H₁₉NO₄*ClH
• Molecular Weight: 349.81
• Product Categories: Amino Acids
• Mol File: 6327-59-9.mol

Chemical Properties

• Melting Point: 124-125 °C
• Boiling Point: 455.3°C at 760 mmHg
• Flash Point: 180.6°C
• Appearance: /Solid
• Density: 1.205g/cm³
• Vapor Pressure: 1.78E-08mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: H-ASP(OBZL)-OBZL HCL(CAS DataBase Reference)
• NIST Chemistry Reference: H-ASP(OBZL)-OBZL HCL(6327-59-9)
• EPA Substance Registry System: H-ASP(OBZL)-OBZL HCL(6327-59-9)

Safety Data

• Hazardous Substances Data: 6327-59-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
H-ASP(OBZL)-OBZL HCL is used as a building block in peptide synthesis for the development of new pharmaceutical compounds. Its Fmoc protection allows for the controlled addition of amino acids during the synthesis process, enabling the creation of complex peptide structures with specific therapeutic properties.
Used in Biochemical Research:
In biochemical research, H-ASP(OBZL)-OBZL HCL is utilized as a key component in the synthesis of peptides for studying their structure, function, and interactions with other biomolecules. The Fmoc protection ensures that the amino acid is incorporated correctly into the peptide sequence, facilitating the investigation of peptide-based mechanisms and their potential applications in medicine and biotechnology.
Used in Solid-Phase Peptide Chemistry:
H-ASP(OBZL)-OBZL HCL is employed as a crucial building block in solid-phase peptide chemistry, a technique that allows for the stepwise assembly of peptides on an insoluble support. The Fmoc group's protective role ensures that the amino acid is added in a controlled manner, enabling the synthesis of peptides with high purity and yield.
Used in Drug Development:
H-ASP(OBZL)-OBZL HCL is used in drug development as a component of peptides with potential therapeutic applications. H-ASP(OBZL)-OBZL HCL's Fmoc protection allows for the precise synthesis of bioactive peptides, which can be further modified and optimized for specific medical uses, such as targeting diseases or modulating biological processes.
Used in Peptide Synthesis Education:
In educational settings, H-ASP(OBZL)-OBZL HCL serves as a practical tool for teaching the principles of peptide synthesis and the importance of protecting groups like Fmoc. Students can gain hands-on experience in synthesizing peptides using this compound, understanding the challenges and techniques involved in the process.

InChI:InChI=1/C18H19NO4/c19-16(18(21)23-13-15-9-5-2-6-10-15)11-17(20)22-12-14-7-3-1-4-8-14/h1-10,16H,11-13,19H2

Upstream product

• 80974-42-1 (S)-N-tert-butyloxycarbonylaspartic acid dibenzyl ester 
• 7536-58-5 BOC-L-aspartic acid 4-benzyl ester 
• 2886-33-1 dibenzyl L-aspartate toluene-4-sulphonate 
• 104-15-4 toluene-4-sulfonic acid 
• 56-84-8 L-Aspartic acid 
• 100-51-6 benzyl alcohol 

Downstream Products

• 122517-23-1 N-(N^α-benzyloxycarbonyl-N^ω-nitro-L-arginyl)-L-aspartic acid dibenzyl ester 
• 7362-93-8 (S)-3-amino-4-(benzyloxy)-4-oxobutanoic acid 
• 79974-09-7 (S)-2-{(S)-4-Benzyloxycarbonyl-4-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-succinic acid dibenzyl ester 
• 79974-12-2 (S)-2-{(S)-4-Benzyloxycarbonyl-2-[4-(benzyloxycarbonyl-methyl-amino)-benzoylamino]-butyrylamino}-succinic acid dibenzyl ester 
• 1025873-02-2 C₂₃H₂₈N₂O₈S 
• 104870-31-7 dibenzyl (2S)-2-({(2S)-4-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoyl}amino)butanedioate 
• 911429-70-4 (1R,2R,6R,8R,12S,14S)-12-benzyloxycarbonylmethyl-10,13-diaza-4,4-dimethyl-16,16-dioxide-11-oxo-3,5,7,17-tetraoxa-16-thio-pentacyclo[9.6.0.0^2,6.0^1,14.0^10,14]heptadecane 
• 1246972-75-7 N-(3-benzyloxycarbonyl-β-carbolin-1-yl)ethyl-L-aspartic acid dibenzyl ester 
• 1283599-32-5 C₃₂H₂₁NO₉ 
• 1283599-53-0 C₃₂H₂₃NO₁₀ 
• 1283599-60-9 C₅₀H₃₈N₂O₁₂ 
• 871266-67-0 dibenzyl (S)-2-{2-[5-(5-carbamimidoyl-1H-benzimidazol-2-yl)-6,2'-dihydroxy-5'-sulfamoylbiphenyl-3-yl]acetylamino}succinate 

Relevant articles and documents

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.

Chirospecific Synthesis of (1S,3R)-1-Amino-3-(hydroxymethyl)cyclopentane, Precursor for Carbocyclic Nucleoside Synthesis. Dieckmann Cyclization with an α-Amino Acid

Carbocyclic nucleosides are important isosters of nucleosides possessing a variety of antiviral and antineoplastic activities.We report here a new method for the chirospecific synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane.This compound is a key precursor for the synthesis of some carbocyclic nucleosides.The method involves (1) an improved synthesis of (S)-2-aminoadipic acid; (2) Dieckmann cyclization of this α-amino acid to an aminocyclopentanone; and (3) elaboration of the latter to the target (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane.The starting (S)-2-aminoadipic acid δ-methyl ester was prepared enantiomerically pure from (S)-aspartic acid in 51percent overall yield.Dieckmann condensation converted this amino acid to a (methoxycarbonyl)-cyclopentanone, and reduction of the ketone followed by elimination yielded (S)-3--1-(methoxycarbonyl)cyclopentene.Reduction of the double bond gave a mixture of the cis and trans diastereomers.This mixture was converted to a single diastereomer by epimerization and trapping of the cis isomer as (1S,4R)-2-(9-phenylfluoren-9-yl)-2-azabicycloheptan-3-one.Hydrolytic cleavage of the lactam followed by reduction gave (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane.