78739-01-2

Basic information

• Product Name: D-AP4
• Synonyms: D-AP4;D(-)-2-AMINO-4-PHOSPHONOBUTYRIC ACID 97%;(2R)-2-Amino-4-phosphonobutyric acid;D(-)-2-Amino-4-phosphonobutyric acid,97%;D(-)-2-Amino-4-phosphonobutyric acidD-AP4;DLGAP4;DLP4;KIAA0964
• CAS NO: 78739-01-2
• Molecular Formula: C₄H₁₀NO₅P
• Molecular Weight: 183.1
• Product Categories: Glutamate receptor
• Mol File: 78739-01-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 491.7 °C at 760 mmHg
• Flash Point: 251.2 °C
• Appearance: white to off-white powder
• Density: 1.628g/cm³
• Vapor Pressure: 5.18E-11mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: 0-6°C
• Solubility: Aqueous Acid (Slightly), Water (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: D-AP4(CAS DataBase Reference)
• NIST Chemistry Reference: D-AP4(78739-01-2)
• EPA Substance Registry System: D-AP4(78739-01-2)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 78739-01-2(Hazardous Substances Data)

Usage

Description

D-AP4, also known as D(-)-2-Amino-4-phosphonobutanoic acid, is an NMDA broad-spectrum excitatory amino acid receptor antagonist. It is a white to off-white powder in its chemical form.

Uses

Used in Pharmaceutical Industry:
D-AP4 is used as a pharmaceutical agent for its neuroprotective properties. It acts as an antagonist of the NMDA receptor, which is involved in various neurological disorders and conditions. By blocking the receptor, D-AP4 can help prevent excitotoxicity and protect neurons from damage.
Used in Research Applications:
D-AP4 is used as a research tool for studying the role of NMDA receptors in the central nervous system. It can help researchers understand the mechanisms of action and potential therapeutic applications of NMDA receptor antagonists in various neurological conditions.
Used in Neurological Disorders Treatment:
D-AP4 is used as a potential treatment for neurological disorders associated with excessive NMDA receptor activity, such as Alzheimer's disease, Parkinson's disease, and Huntington's disease. Its neuroprotective effects can help slow down the progression of these disorders and improve the quality of life for patients.
Used in Neurotrauma and Brain Injury:
D-AP4 is used as a potential treatment for neurotrauma and brain injury, where excessive NMDA receptor activity can lead to secondary damage and neuronal death. By blocking the NMDA receptor, D-AP4 can help reduce the extent of injury and promote recovery.

Biological Activity

Broad spectrum excitatory amino acid receptor antagonist. Also agonist at the quisqualate-sensitized AP6 site in hippocampus where it is less potent than L-AP4.

InChI:InChI=1/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m1/s1

Upstream product

• 141894-89-5 S(+)-2-amino-4-diethoxyphosphonobutanoic acid 
• 104738-93-4 methyl (R)-(-)-2-amino-4-(diethoxyphosphoryl)butanoate 
• 141894-89-5 2(R)-amino-4-(diethoxyphosphoryl)butanoic acid 
• 86554-31-6 2-Amino-4-(dimethoxy-phosphoryl)-butyric acid methyl ester 

Relevant articles and documents

Enantioselective synthesis of (S)-2-amino-3-phosphonopropionic acid, (S)-AP-3, and (R)-2-amino-4-phosphonobutanoic acid, (R)-AP-4, via diastereoselective azidation of (4R,5R)-trans-N-[(diethoxyphosphoryl)propionyl]- and (4R,5R)-trans-N-[(diethoxyphosphoryl)butanoyl]hexahydrobenzoxazolidin-2-one

N-Acylation of readily available, enantiopure oxazolidinone (4R,5R)-1b with (diethoxyphosphoryl)propionyl chloride and (diethoxyphosphoryl)butanoyl chloride affords de title substrates (4R,5R)-2 and (4R,5R)-7, respectively, which are azidated with high diastereoselectivity by means of the reaction between their sodium enolates (4R,5R)-2-Na and (4R,5R)-7-Na with trisyl azide. Removal of the chiral auxiliary from azidated products (4R,5R,2′S)-3 and (4R,5R,2′R)-8 followed by hydrogenation and hydrolysis of the resulting carboxylic acids (S)-4 and (R)-9 gave the pharmacologically relevant aminophosphonic acids (S)-AP-3 and (R)-AP-4 in good yield.

Involucrin gene expression promoter

PROBLEM TO BE SOLVED: To provide an involucrin gene expression promoter that has high effect of promoting involucrin gene expression, and is applied to the skin, to quickly increase involucrin concentrations, and markedly improving the barrier function. SOLUTION: An involucrin gene expression promoter contains at least one selected from a compound represented by the following formula (1) [where R1 and R2 are the same or different to represent a hydrogen atom, or a substituent. n is an integer of 1 or greater], a salt thereof, and their hydrates as an active ingredient. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPO&INPIT

Asymmetric Syntheses via Heterocyclic Intermediates, XXXI.- Asymmetric Synthesis of Various Non-Proteinogenic Amino Acid Methyl Esters (Functionalized in the Carbon Chain) and Amino Acids by the Bislactim Ether Method

The lithiated bislactim ethers 5, 10, 12, and 23 were alkylated with a variety of alkylating agents 6 to give the alkylated bislactim ethers 7, 11, 13, and 24 with a high degree of asymmetric induction (up to 99percent).Upon hydrolysis these furnished the optically active amino acid methyl esters of type 8, 14, or 25.Some of these amino acid esters were further hydrolyzed to yield the amino acids.