3343-29-1

Basic information

• Product Name: N-ALPHA-PHTHALYL-L-GLUTAMINE
• Synonyms: 4-CARBAMOYL-2-(1,3-DIOXO-1,3-DIHYDRO-ISOINDOL-2-YL)-BUTYRIC ACID;PHT-GLN-OH;PHTHALOYL-L-GLUTAMINE;PHTHALYL-L-GLUTAMINE;N-ALPHA-PHTHALYL-L-GLUTAMINE;N-α-Phthalyl-L-glutamine;2H-Isoindole-2-acetic acid, .alpha.-(3-amino-3-oxopropyl)-1,3-dihydro-1,3-dioxo-, (.alpha.S)-
• CAS NO: 3343-29-1
• Molecular Formula: C₁₃H₁₂N₂O₅
• Molecular Weight: 276.24
• Mol File: 3343-29-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 163 °C
• Boiling Point: 599.3°Cat760mmHg
• Flash Point: 316.3°C
• Appearance: /
• Density: 1.508g/cm³
• Vapor Pressure: 3.27E-15mmHg at 25°C
• Refractive Index: 1.639
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.47±0.10(Predicted)
• CAS DataBase Reference: N-ALPHA-PHTHALYL-L-GLUTAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ALPHA-PHTHALYL-L-GLUTAMINE(3343-29-1)
• EPA Substance Registry System: N-ALPHA-PHTHALYL-L-GLUTAMINE(3343-29-1)

Safety Data

• Hazardous Substances Data: 3343-29-1(Hazardous Substances Data)

Usage

General Description

N-Alpha-Phthalyl-L-Glutamine, also known as PALG, is a chemical compound that is commonly used as a protective reagent for the amino group of glutamine. It is often utilized in the synthesis of peptides and as a protecting group for the amino acid in peptide chemistry. PALG is known for its stability and selectivity, making it an ideal reagent for the protection of the glutamine amino group in peptide synthesis. Its use allows for efficient and precise manipulation of peptide sequences, making it a valuable tool in the field of organic chemistry and drug development. Additionally, PALG has been studied for its potential use in the treatment of neurodegenerative diseases and as a prodrug for targeted drug delivery.

InChI:InChI=1/C13H12N2O5/c14-10(16)6-5-9(13(19)20)15-11(17)7-3-1-2-4-8(7)12(15)18/h1-4,9H,5-6H2,(H2,14,16)(H,19,20)/t9-/m0/s1

Upstream product

• 56-85-9 L-glutamine 
• 22509-74-6 N-ethoxycarbonylphthalimide 
• 85-44-9 phthalic anhydride 
• 841-67-8 (S)-thalidomide 
• 25830-77-7 N-phthaloyl-L-glutamic anhydride 

Downstream Products

• 50-35-1 thalidomide 
• 73-22-3 L-Tryptophan 

Relevant articles and documents

CRYSTALLINE FORMS OF THALIDOMIDE AND PROCESSES FOR THEIR PREPARATION

The present invention relates to crystalline forms of thalidomide having a high polymorphic purity and to processes for their preparation. The present invention also relates to pharmaceutical preparations comprising the crystalline forms for the treatment of patients suffering from autoimmune, inflammatory or angiogenic disorders.

AN IMPROVED PROCESS FOR THE PREPARATION OF THALIDOMIDE

An improved process for the preparation of Thalidomide a TNF-alpha inhibitor by the conversion of N-phthaloyl L-glutamine in presence of an active ingredient of inorganic acid salts such as 1,1-Carbonyldi(1,2,4-triazole) as a condensing agent.

Chiral inversion and hydrolysis of thalidomide: Mechanisms and catalysis by bases and serum albumin, and chiral stability of teratogenic metabolites

The chiral inversion and hydrolysis of thalidomide and the catalysis by bases and human serum albumin were investigated by using a stereoselective HPLC assay. Chiral inversion was catalyzed by albumin, hydroxyl ions, phosphate, and amino acids. Basic amino acids (Arg and Lys) had a superior potency in cataLyzing chiral inversion compared to acid and neutral ones. The chiral inversion of thalidomide is thus subject to Specific and general base catalysis, and it is suggested that the ability of HSA to catalyze the reaction is due to the basic groups of the amino acids Arg and Lys and not to a single catalytic site on the macromolecule. The hydrolysis of thalidomide was also base-catalyzed. However, albumin had no effect on hydrolysis, and there was no difference between the catalytic potencies of acidic, neutral, and basic amino acids. This may be explained by different reaction mechanisms of the chiral inversion and hydrolysis of thalidomide. Chiral inversion is deduced to occur by electrophilic substitution involving specific and general base catalysis, whereas hydrolysis is thought to occur by nucleophilic substitution involving specific and general base as well as nucleophilic catalysis. As nucleophilic attack is sensitive to steric properties of the catalyst, steric hindrance might be the reason albumin is not able to catalyze hydrolysis. 1H NMR experiments revealed that the three teratogenic metabolites of thalidomide, in sharp contrast to the drug itself, had complete chiral stability. This leads to the speculation that, were some enantioselectivity to exist in the teratogenicity of thalidomide, it could result from fast hydrolysis to chirally stable teratogenic metabolites.