162870-29-3

Basic information

• Product Name: (S)-3,5-DIHYDROXYPHENYLGLYCINE
• Synonyms: (S)-3,5-DIHYDROXYPHENYLGLYCINE;(S)-3,5-DHPG;S-DHPG;(S)-3,5-Dihydroxyphenylglycine hydrate;(S)-3,5-Dihydroxylphenylglycine
• CAS NO: 162870-29-3
• Molecular Formula: C8H9NO4
• Molecular Weight: 183.16
• EINECS: 2017-001-1
• Product Categories: Glutamate receptor;Glutamate
• Mol File: 162870-29-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 448.8±33.0 °C(Predicted)
• Appearance: white/solid
• Density: 1.550±0.06 g/cm3(Predicted)
• Storage Temp.: −20°C
• Solubility: Aqueous Base (Very Slightly, Sonicated), Methanol (Slightly), Water (Slightly, H
• PKA: 1.77±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: (S)-3,5-DIHYDROXYPHENYLGLYCINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3,5-DIHYDROXYPHENYLGLYCINE(162870-29-3)
• EPA Substance Registry System: (S)-3,5-DIHYDROXYPHENYLGLYCINE(162870-29-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 162870-29-3(Hazardous Substances Data)

Usage

Description

(S)-3,5-Dihydroxyphenylglycine, also known as (S)-DHPG, is an organic compound that serves as a potent agonist for group I metabotropic glutamate receptors, specifically mGluR1 and mGluR5. It plays a significant role in the treatment of neuronal injury and cognitive enhancement due to its ability to activate specific receptors in the brain.

Uses

Used in Pharmaceutical Industry:
(S)-3,5-Dihydroxyphenylglycine is used as a therapeutic agent for the treatment of neuronal injury. It aids in the recovery process by targeting and activating specific metabotropic glutamate receptors, which are crucial for neuronal function and synaptic plasticity.
Used in Cognitive Enhancement:
(S)-3,5-Dihydroxyphenylglycine is used as a cognitive enhancer to improve memory and cognitive function. By acting as an agonist for mGluR1 and mGluR5 receptors, it modulates synaptic transmission and plasticity, leading to enhanced cognitive performance.
Used in Neuroscience Research:
(S)-3,5-Dihydroxyphenylglycine hydrate is used as an mGluR1/5 agonist in synaptoneurosomal preparations for DHPG stimulation. It is injected into the basolateral amygdala to study its effects on memory expression, providing valuable insights into the underlying mechanisms of memory and learning processes.

Biological Activity

Selective group I mGlu receptor agonist. Also available as part of the Group I mGlu Receptor Tocriset? and Mixed mGlu Receptor Tocriset? .

Biochem/physiol Actions

(S)-3,5-Dihydroxyphenylglycine hydrate is a group I metabotropic glutamate receptor agonist.

Upstream product

• 1208237-23-3 2-amino-2-(3,5-dihydroxyphenyl)acetonitrile 
• 187979-09-5 (R)-(3,5-Dihydroxy-phenyl)-ureido-acetic acid 
• 116435-46-2 5-(3,5-Dimethoxy-phenyl)-imidazolidine-2,4-dione 
• 187978-82-1 5-(3',5'-dihydroxyphenyl)hydantoin 
• 7311-34-4 3,5-dimethoxybenzaldehdye 

Downstream Products

• 1598416-01-3 Fmoc-D-Dpg-OH 

Relevant articles and documents

Large α-aminonitrilase activity screening of nitrilase superfamily members: Access to conversion and enantiospecificity by LC-MS

A high-throughput screening for the identification of nitrilases demonstrating activity towards alpha-aminonitriles is reported. A LC-MS assay giving access to both conversion and enantiospecificity was developed. 588 candidate enzymes were screened as cell lysates against six alpha-aminonitriles in 96-well microplates. The candidate enzymes were selected following two criteria, their sequence identity with a set of known nitrilases or their phylogenetic position among the nitrilase superfamily. Five enzymes were identified and found to hydrolyse alpha-aminonitrile into the corresponding alpha-aminoacid. The substrate range was found to be very narrow as only two different alpha-aminonitriles, 2-aminovaleronitrile and 2-amino-2- phenylacetonitrile, were found to be substrates. The biocatalytic capabilities of three enzymes were further investigated and the best result was obtained with an enzyme from Burkholderia xenovorans catalysing the enantiospecific hydrolysis of 2-aminovaleronitrile into (S)-norvaline with excellent conversion and enantiomeric excess.

New antiviral antibiotics, kistamicins A and B. II. Structure determination

The structures of antiviral antibiotics kistamicins A and B have been determined by a combination of chemical degradation and spectral analysis. They are commonly composed of D-tyrosine 3,5-dihydrophenylglycine a biphenyl ether bis-amino acid and a diphenyl substituted indole tris-amino acid forming a tricyclic ring structure. Kistamicin B possessed a phenethylamide at the amino terminal of kistamicin A. They are structurally related to the nuclei of the vancomycin group antibiotics particularly to antibiotic complestatin.