13523-75-6

Basic information

• Product Name: (2S)-2-amino-5-oxo-5-(2-phenylhydrazinyl)pentanoic acid (non-preferred name)
• CAS NO: 13523-75-6
• Molecular Formula: C₁₁H₁₅N₃O₃
• Molecular Weight: 237.2551
• Mol File: 13523-75-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 414°C at 760 mmHg
• Flash Point: 204.2°C
• Density: 1.321g/cm³
• Vapor Pressure: 1.35E-07mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: (2S)-2-amino-5-oxo-5-(2-phenylhydrazinyl)pentanoic acid (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-amino-5-oxo-5-(2-phenylhydrazinyl)pentanoic acid (non-preferred name)(13523-75-6)
• EPA Substance Registry System: (2S)-2-amino-5-oxo-5-(2-phenylhydrazinyl)pentanoic acid (non-preferred name)(13523-75-6)

Safety Data

• Hazardous Substances Data: 13523-75-6(Hazardous Substances Data)

Usage

General Description

(2S)-2-amino-5-oxo-5-(2-phenylhydrazinyl)pentanoic acid, also known as 2-aminoglutarylphenylhydrazide, is a chemical compound with a molecular formula C11H16N2O3. It is a derivative of L-glutamic acid and is used in the field of biochemistry and molecular biology. (2S)-2-amino-5-oxo-5-(2-phenylhydrazinyl)pentanoic acid (non-preferred name) is commonly used as a reagent in the synthesis of peptide and protein compounds. It is also used in the study of enzyme-mediated reactions and as a substrate for various enzymatic assays. Additionally, (2S)-2-amino-5-oxo-5-(2-phenylhydrazinyl)pentanoic acid has been studied for its potential pharmacological properties, including its role in modulating neuronal function and potentially serving as a treatment for neurodegenerative diseases.

Upstream product

• 100-63-0 phenylhydrazine 
• 98-79-3 L-Pyroglutamic acid 
• 149-87-1 Pyroglutamic acid 

Relevant articles and documents

γ-Glutamyl transpeptidase-dependent mutagenicity and cytotoxicity of γ-Glutamyl derivatives: A model for biochemical targeting of chemotherapeutic agents

Many carcinomas in humans are rich in glutamyl transpeptidase (GGT), a plasma membrane enzyme that reacts with extracellular substrates. Thus, biochemical targeting of chemotherapeutic agents may be achieved by converting anticancer drugs into their γ-glutamyl derivatives. Chemical conversion of phenylhydrazine (PH) and biochemical modification of daunomycin (DM) into their γ-glutamyl derivatives γ-glutamyl phenylhydrazine (GGPH) and γ-glutamyl DM (GGDM) resulted in the abolishment of their mutagenicity and cytotoxicity, as judged by decreased viability and increased mutant yields in cultures of several Salmonella Ames strains. Commercial γ- glutamyl-p-nitroanilide (GGPNA) was not toxic or mutagenic. Mutagenicity and/or cytotoxicity of these γ-glutamyl derivatives were restored upon reaction with GGT, with concomitant release of PH, and p-nitroaniline (PNA). The GGT-dependent release of DM from GGDM was demonstrated by thin layer chromatography (TLC), spectral analysis, and specific mutagenicity. Mutagenicity and/or cytotoxicity of γ-glutamyl derivatives increased in the presence of glycylglycine, a GGT activator, and decreased in the presence of serine-borate, a GGT inhibitor. GGDM retained considerable DNA binding capacity. Its inability to kilt and mutagenize was due to altered transport properties. The results are compatible with the notion that γ-glutamylation is a feasible method for biochemical targeting of drugs containing a primary amino group to GGT-rich tumors.