79055-68-8

Basic information

• Product Name: D-AP5
• Synonyms: D-AP5;D-(-)-2-AMINO-5-PHOSPHONOPENTANOIC ACID;D-2-AMINO-5-PHOSPHONOPENTANOIC ACID;D-(-)-2-AMINO-5-PHOSPHONOVALERIC ACID;D(-)-2-Amino-5-phosphonovaleric acid hydrate;D-(-)-2-AMINO-5-PHOSPHONOPENTANOIC ACID (D-AP5);D(-)-AP-5, D(-)-APV, D-2-Amino-5-phosphonovaleric acid;(2R)-2-Amino-5-phosphonovaleric acid
• CAS NO: 79055-68-8
• Molecular Formula: C5H12NO5P
• Molecular Weight: 197.13
• Product Categories: Glutamate receptor;Glutamate
• Mol File: 79055-68-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: approximate 233℃
• Boiling Point: 482.1 °C at 760 mmHg
• Flash Point: 245.4 °C
• Appearance: white fine crystalline powder
• Density: 1.529 g/cm³
• Vapor Pressure: 1.28E-10mmHg at 25°C
• Storage Temp.: Store at RT
• Solubility: Soluble to 100 mM in sterile
• PKA: 2.46±0.10(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: D-AP5(CAS DataBase Reference)
• NIST Chemistry Reference: D-AP5(79055-68-8)
• EPA Substance Registry System: D-AP5(79055-68-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: RD2513000
• Hazardous Substances Data: 79055-68-8(Hazardous Substances Data)

Usage

Description

D-AP5 is a selective N-methyl-D-aspartate (NMDA) receptor antagonist (Kd = 1.4 μM) that competitively inhibits the glutamate binding site of NMDA receptors. Whereas D-AP5 is the active (?)-stereoisomer, its (+)-isomer (L-AP5) demonstrates considerably less potent NMDA receptor antagonist activity. AP5 has been widely used to study the activity of NMDA receptors particularly in regard to researching synaptic plasticity, learning, and memory.

Chemical Properties

white fine crystalline powder

Uses

A competitive NMDA antagonist

General Description

Active enantiomer of DL-2-amino-5-phosphonopentanoic acid (AP5) that is a commonly used competitive NMDA receptor antagonist.

Biological Activity

Widely used competitive NMDA antagonist. More active form of AP5. Also agonist at quisqualate-sensitized AP6 site where it is less potent than the L-isomer (L-(+)-2-Amino-5-phosphonopentanoic acid ). Also available as part of the Mixed NMDA Receptor Tocriset? .

Biochem/physiol Actions

Product does not compete with ATP.

InChI:InChI=1/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)/p-2/t4-/m1/s1

Upstream product

• 76326-31-3 APV 
• 149917-69-1 (R)-tert-butyl 4-(3-(diethoxyphosphoryl)propyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 119878-91-0 (E)-3-(3-(diethylphosphono)prop-2-en-1-yl)-4-(tert-butoxycarbonyl)-5-phenyl-2H-1,4-oxazin-2-one 
• 118492-04-9 (-)-(2R,3E)-2-amino-5-phosphono-3-pentenoic acid 

Relevant articles and documents

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 synthesis of D-(E)-2-amino-5-phosphono-3-pentenoic acid (APPA) by using a chiral auxiliary

The synthesis of D-2-amino-5-phosphono-3-pentenoic acid (1) is reported. The key intermediate, a (2R,3S)-3-hydroxyallylglycine derivative (8), was prepared by the reaction of (5S)-3,6-dimethoxy-5-isopropyl-2,4-dihydropyrazine (2) and acrolein in the presence of chlorotitanium tris(diethylamide). The transformation of 8 into 1 via allylic alcohol 11 was carried out by following the reported route.

A new method for the preparation of (2R)-2-amino-5-phosphonopentanoic acid

A new and efficient synthesis of (2R)-2-amino-5-phosphonopentanoic acid(AP5) is reported. Our approach is based on a pseudo-Claisen [2,3] sigmatropic rearrangement of an alkyne phosphite.