2614-08-6

Basic information

• Product Name: (4S)-5-amino-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid
• CAS NO: 2614-08-6
• Molecular Formula: C₁₃H₁₂N₂O₅
• Molecular Weight: 276.2448
• Mol File: 2614-08-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 583.8°C at 760 mmHg
• Flash Point: 306.9°C
• Density: 1.508g/cm³
• Vapor Pressure: 1.8E-14mmHg at 25°C
• Refractive Index: 1.639
• CAS DataBase Reference: (4S)-5-amino-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-5-amino-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid(2614-08-6)
• EPA Substance Registry System: (4S)-5-amino-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid(2614-08-6)

Safety Data

• Hazardous Substances Data: 2614-08-6(Hazardous Substances Data)

Usage

Description

(4S)-5-amino-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid is a derivative of isoindoline, a heterocyclic compound with a 1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl group attached to a pentanoic acid. It contains an amino group and a ketone group, making it a versatile compound for various chemical reactions and biological processes.

Uses

Used in Medicinal Chemistry:
(4S)-5-amino-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid is used as a building block for the synthesis of pharmaceuticals due to its versatile chemical structure and the presence of functional groups that can be utilized in various reactions.
Used in Drug Discovery and Development:
(4S)-5-amino-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid is used as a tool compound for studying biological pathways related to isoindoline derivatives, which could potentially lead to the discovery and development of new drugs targeting these pathways.
Used in Research and Characterization:
(4S)-5-amino-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid is used as a research compound to further investigate its properties, reactivity, and potential applications in various fields, including pharmaceuticals and biochemistry.

Upstream product

• 841-67-8 (S)-thalidomide 
• 85-44-9 phthalic anhydride 
• 636-65-7 glutamine 

Relevant articles and documents

LC–MS/MS and chiroptical spectroscopic analyses of multidimensional metabolic systems of chiral thalidomide and its derivatives

Enantiomeric thalidomide undergoes various kinds of biotransformations including chiral inversion, hydrolysis, and enzymatic oxidation, which results in several metabolites, thereby adding to the complexity in the understanding of the nature of thalidomide. To decipher this complexity, we analyzed the multidimensional metabolic reaction networks of thalidomide and related molecules in vitro. Characteristic patterns in the amount of various metabolites of thalidomide and related molecules generated during a combination of chiral inversion, hydrolysis, and hydroxylation were observed using liquid chromatography–tandem mass spectrometry and chiroptical spectroscopy. We found that monosubstituted thalidomide derivatives exhibited different time-dependent metabolic patterns compared with thalidomide. We also revealed that monohydrolyzed and monohydroxylated metabolites of thalidomide were likely to generate mainly by a C-5 oxidation of thalidomide and subsequent ring opening of the hydroxylated metabolite. Since chirality was conserved in most of these metabolites during metabolism, they had the same chirality as that of nonmetabolized thalidomide. Our findings will contribute toward understanding the significant pharmacological effects of the multiple metabolites of thalidomide and its derivatives.

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.