76326-31-3

Basic information

• Product Name: DL-2-AMINO-5-PHOSPHONOPENTANOIC ACID
• Synonyms: APV;AP-5;DL-2-AMINO-5-PHOSPHONOVALERIC ACID;DL-2-AMINO-5-PHOSPHONOPENTANOIC ACID;DL-AP5;5-PHOSPHONO-DL-NORVALINE;(+/-)-2-AMINO-5-PHOSPHONO-PENTANOIC ACID;DL-2-AMINO-5-PHOSPHONOPENTANOIC ACID (DL-AP5)
• CAS NO: 76326-31-3
• Molecular Formula: C₅H₁₂NO₅P
• Molecular Weight: 197.13
• Product Categories: Glutamate receptor;Glutamate
• Mol File: 76326-31-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 482.1 °C at 760 mmHg
• Flash Point: 245.4 °C
• Appearance: white/solid
• Density: 1.529 g/cm³
• Vapor Pressure: 1.28E-10mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: Store at RT
• Solubility: NH4OH 1 M: 50 mg/mL, clear, colorless
• PKA: 2.46±0.10(Predicted)
• BRN: 2446389
• CAS DataBase Reference: DL-2-AMINO-5-PHOSPHONOPENTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: DL-2-AMINO-5-PHOSPHONOPENTANOIC ACID(76326-31-3)
• EPA Substance Registry System: DL-2-AMINO-5-PHOSPHONOPENTANOIC ACID(76326-31-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 76326-31-3(Hazardous Substances Data)

Usage

Uses

DL-2-Amino-5-phosphonopentanoic acid has been used:in the inactivation of N-methyl-D-aspartate (NMDA)-mediated synapsesused in growth medium for inhibition of electrical activity in the neuronal networkused to isolate N-methyl-D-aspartate receptors (NMDAR) or α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (AMPAR)-mediated currents were isolated using this productused in double distilled water to compare its NMDA antagonistic action with that of prion protein (PrPC)

Definition

ChEBI: The 5-phosphono derivative of 2-aminopentanoic acid; acts as an N-methyl-D-aspartate receptor antagonist.

Biological Activity

Potent NMDA antagonist. See separate isomers (D-(-)-2-Amino-5-phosphonopentanoic acid and L-(+)-2-Amino-5-phosphonopentanoic acid ).

Biochem/physiol Actions

Anticonvulsant; potent and selective NMDA receptor antagonist.

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)/t4-/m0/s1

Upstream product

• 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 
• 79055-67-7 (S)-2-amino-5-phosphonopentanoic acid 
• 95306-95-9 2-Acetylamino-2-[3-(diethoxy-phosphoryl)-propyl]-malonic acid diethyl ester 

Downstream Products

• 76326-31-3 AP-5 
• 113811-43-1 N-(4-amino-4-deoxypteroyl)-DL-2-amino-5-phosphonopentanoic acid 
• 113811-53-3 benzyl DL-2-amino-5-phosphonopentanoate 
• 258278-51-2 2-(N-phenylacetylamino)-5-phosphonovaleric acid 

Relevant articles and documents

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.

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

Phosphorus-containing aminocarboxylic acids. VI. Improved synthesis of 2-amino-5-phosphonopentanoic acid

An improved three-step procedure for the synthesis of 2-amino-5-phosphonopentanoic acid is proposed.