254737-29-6

Basic information

• Product Name: 2-(3-Sulfanylpropyl)pentanedioic acid
• Synonyms: 2-MPPA; GPI-5693; NAAL-1
• CAS NO: 254737-29-6
• Molecular Formula: C₈H₁₄O₄S
• Molecular Weight: 206.26238
• Mol File: 254737-29-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-(3-Sulfanylpropyl)pentanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-Sulfanylpropyl)pentanedioic acid(254737-29-6)
• EPA Substance Registry System: 2-(3-Sulfanylpropyl)pentanedioic acid(254737-29-6)

Safety Data

• Hazardous Substances Data: 254737-29-6(Hazardous Substances Data)

Usage

Type of compound

Carboxylic acid with a thiol group (thiolactic acid)

Functional groups

Two carboxylic acid groups (-COOH) and one thiol group (-SH)

Importance

An intermediate compound in the biosynthesis of coenzyme A and plays a critical role in the metabolism of fatty acids and other important biochemical processes

Usage

Commonly used in the field of organic synthesis and biochemistry for its ability to form complexes with metal ions and for its reactivity in thiol exchange reactions

Potential applications

Pharmaceutical and cosmetic industries due to its biological activity and potential therapeutic effects.

Upstream product

• 254737-41-2 2,2-dimethyl-4,6-dioxo-5-[3-[(triphenyl-methyl)thio]propyl]-1,3-dioxane-5-propanoic acid methyl ester 
• 254737-42-3 6-[(triphenylmethyl)thio]-1,3,3-hexanetricarboxylic acid 
• 254737-40-1 2,2-dimethyl-5-[3-[(triphenylmethyl)thio]propyl]-[1,3]dioxane-4,6-dione 
• 757246-49-4 3-(2-oxotetrahydro-2H-thiopyran-3-yl)propionic acid 
• 848952-59-0 (R)-3-(2-oxo-tetrahydro-thiopyran-3-yl)propionic acid 
• 254737-43-4 6-[(triphenylmethyl)thio]-1,3-hexanedicarboxylic acid 

Relevant articles and documents

Enantiospecificity of glutamate carboxypeptidase II inhibition

Two representative glutamate carboxypeptidase II (GCP II) inhibitors, 2-(hydroxypentafluorophenylmethyl-phosphinoylmethyl)pentanedioic acid 2 and 2-(3-mercaptopropyl)pentanedioic acid 3, were synthesized in high optical purities (>97%ee). The two enantiom

Synthesis and biological evaluation of thiol-based inhibitors of glutamate carboxypeptidase II: Discovery of an orally active GCP II inhibitor

A series of 2-(thioalkyl)pentanedioic acids were synthesized and evaluated as inhibitors of glutamate carboxypeptidase II (GCP II, EC 3.4.17.21). The inhibitory potency of these thiol-based compounds against GCP II was found to be dependent on the number of methylene units between the thiol group and pentanedioic acid. A comparison of the SAR of the thiol-based inhibitors to that of the phosphonate-based inhibitors provides insight into the role of each of the two zinc-binding groups in GCP II inhibition. The most potent thiol-based inhibitor, 2-(3-mercaptopropyl)pentanedioic acid (IC50 = 90 nM), was found to be orally bioavailable in rats and exhibited efficacy in an animal model of neuropathic pain following oral administration.

NAALADase inhibitors useful as pharmaceutical compounds and compositions

The present invention relates to N-Acetylated α-Linked Acidic Dipeptidase (NAALADase) inhibitors enzyme activity, pharmaceutical compositions comprising such inhibitors, and methods of their use to inhibit NAALADase enzyme activity, thereby effecting neur