400625-57-2

Basic information

• Product Name: (2R,4R)-2-AMINO-4-THIOPHEN-2-YLMETHYL-PENTANEDIOIC ACID
• Synonyms: (4S)-4-(THIOPHEN-2-YLMETHYL)-D-GLUTAMIC ACID;(2R,4S)-2-AMINO-4-THIOPHEN-2-YLMETHYL-PENTANEDIOIC ACID;(2R,4R)-2-AMINO-4-THIOPHEN-2-YLMETHYL-PENTANEDIOIC ACID;D-Glutamic acid, 4-(2-thienylmethyl)-, (4R)-
• CAS NO: 400625-57-2
• Molecular Formula: C10H13NO4S
• Molecular Weight: 243.28
• Mol File: 400625-57-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 456.4°C at 760 mmHg
• Flash Point: 229.8°C
• Appearance: /
• Density: 1.419g/cm³
• Vapor Pressure: 4.03E-09mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: (2R,4R)-2-AMINO-4-THIOPHEN-2-YLMETHYL-PENTANEDIOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-2-AMINO-4-THIOPHEN-2-YLMETHYL-PENTANEDIOIC ACID(400625-57-2)
• EPA Substance Registry System: (2R,4R)-2-AMINO-4-THIOPHEN-2-YLMETHYL-PENTANEDIOIC ACID(400625-57-2)

Safety Data

• Hazardous Substances Data: 400625-57-2(Hazardous Substances Data)

Usage

General Description

(2R,4R)-2-AMINO-4-THIOPHEN-2-YLMETHYL-PENTANEDIOIC ACID is a chemical compound with a molecular formula C10H15NO4S. It is an amino acid derivative with a thiophen-2-ylmethyl group attached to a pentanedioic acid backbone. The molecule contains a chiral center, resulting in two possible stereoisomers. (2R,4R)-2-AMINO-4-THIOPHEN-2-YLMETHYL-PENTANEDIOIC ACID may have potential biological activity due to its structural similarity to natural amino acids, and further research is needed to understand its properties and potential applications.

InChI:InChI=1/C10H13NO4S/c11-8(10(14)15)5-6(9(12)13)4-7-2-1-3-16-7/h1-3,6,8H,4-5,11H2,(H,12,13)(H,14,15)/t6-,8-/m1/s1

Upstream product

• 45438-73-1 2-thenyl bromide 
• 554-14-3 2-Methylthiophene 

Relevant articles and documents

4-Substituted D-glutamic acid analogues: The first potent inhibitors of glutamate racemase (MurI) enzyme with antibacterial activity

The first potent inhibitors of glutamate racemase (MurI) enzyme that show whole cell antibacterial activity are described. Optically pure 4-substituted D-glutamic acid analogues with (2R,4S) stereochemistry and bearing aryl-, heteroaryl-, cinnamyl-, or biaryl-methyl substituents represent a novel class of glutamate racemase inhibitors. Exploration of the D-Glu core led to the identification of lead compounds (-)-8 and 10. 2-Naphthylmethyl derivative 10 was found to be a potent competitive inhibitor of glutamate racemase activity (Ki = 16 nM, circular dichroism assay; IC50 = 0.1 μg/mL high-performance liquid chromatography (HPLC) assay). Thorough structure-activity relationship (SAR) studies led to benzothienyl derivatives such as 69 and 74 with increased potency (IC50 = 0.036 and 0.01 μg/mL, respectively, HPLC assay). These compounds showed potent whole cell antibacterial activity against S. pneumoniae PN-R6, and good correlation with the enzyme assay. Compounds 69, 74 and biaryl derivative 52 showed efficacy in an in vivo murine thigh infection model against Streptococcus pneumoniae. Data described herein suggest that glutamate racemase may be a viable target for developing new antibacterial agents.