79055-67-7

Basic information

• Product Name: L-AP5
• Synonyms: L-AP5;L(+)-2-AMINO-5-PHOSPHONOPENTANOIC ACID;L(+)-2-AMINO-5-PHOSPHONOVALERIC ACID;(2S)-2-Amino-5-phosphonovaleric acid;(S)-5-Phosphono-2-aminovaleric acid;L(+)-2-Amino-5-phosphonovaleric acid,95% ( >99% ee)
• CAS NO: 79055-67-7
• Molecular Formula: C5H12NO5P
• Molecular Weight: 197.13
• Product Categories: Glutamate receptor
• Mol File: 79055-67-7.mol

Chemical Properties

• Melting Point: 105°C
• Boiling Point: 482.1°C at 760 mmHg
• Flash Point: 245.4°C
• Appearance: /solid
• Vapor Pressure: 1.28E-10mmHg at 25°C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: L-AP5(CAS DataBase Reference)
• NIST Chemistry Reference: L-AP5(79055-67-7)
• EPA Substance Registry System: L-AP5(79055-67-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 79055-67-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-AP5 is used as a research chemical for the development of drugs targeting the NMDA receptor, which plays a crucial role in various neurological processes, including learning, memory, and synaptic plasticity. Its antagonistic action on the NMDA receptor makes it a potential candidate for the treatment of neurological disorders such as Alzheimer's disease, Parkinson's disease, and Huntington's disease.
Used in Neuroscience Research:
L-AP5 is used as a research tool in neuroscience to study the role of the NMDA receptor in synaptic transmission, neuronal excitability, and neuroprotection. It helps researchers understand the mechanisms underlying various neurological conditions and develop novel therapeutic strategies.
Used in Drug Discovery and Development:
L-AP5 is used in drug discovery and development as a lead compound for the design and synthesis of new drugs targeting the NMDA receptor. Its unique pharmacological properties make it a valuable template for the development of innovative therapeutic agents with improved efficacy and safety profiles.

Biological Activity

NMDA antagonist. Also agonist at quisqualate-sensitized AP6 site, where it is more potent than the D-isomer (D-(-)-2-Amino-5-phosphonopentanoic acid ).

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-/m0/s1

Upstream product

• 1186-10-3 diethyl 3-(bromopropyl)phosphonic acid 
• 56-40-6 glycine 
• 118492-04-9 (-)-(2R,3E)-2-amino-5-phosphono-3-pentenoic acid 
• 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 

Downstream Products

• 76326-31-3 APV 

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

Phosphorus-containing aminocarboxylic acids. VII. Asymmetric synthesis of ω-phosphono-α-aminocarboxylic acids

New asymmetric ω-phosphono-α-aminocarboxylic acids were synthesized by alkylation with ω-bromoalkylphosphonates of the glycine methylene group in the Ni(II) complex of the Schiff base derived from glycine and (S)- and (R)-2-N-(N-benzylprolyl)-o-aminobenzo

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.

Highly enantioselective synthesis of (R)- and (S)-2-amino-5-phosphonopentanoic acids [(R)- and (S)-AP5] via modified Seebach imidazolidinones

The preparation of four new stereoisomeric 1-carbobenzyloxy-2-tert-butyl-3-(α-methylbenzyl)-1,3-imidazolidin-4-o nes is described. Alkylation of the lithium enolates of these chiral glycine derivatives proceeds with high diastereoselectivity. In particula

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.

Asymmetric Synthesis of Phosphorus Analogues of Dicarboxylic α-Amino Acids

An efficient approach to the asymmetric synthesis of phosphorus analogues of dicarboxylic α-amino acids is described.The method of choice consists in the reaction of the nickel(II) complex (4) of the Schiff's base derived from (S)-o-benzophenone 3 and glycine with the appropriate alkyl halide, substituted with an alkylphosphonate group.The reactions were carried out in MeCN at 25 deg C, with solid KOH as catalyst.Michael-type base-catalysed addition of vinylphosphonate and vinylphosphinate to complex 4 in dimethylformamide (DMF)at 50 - 70 deg C could also be employed.Significant diastereoselectivity (90percent d.e.) was observed for the alkylation of complex 4.Optically pure (S)-phosphinothricine, (S)-2-amino-3-phosphonopropanoic acid, (S)-2-amino-4-phosphonobutanoic acid and (S)-2-amino-5-phosphonopentanoic acid were obtained after the alkylated diastereoisomeric complexes had been separated on SiO2 and hydrolysed with aq.HCl.The initial chiral reagent 3 was recovered (60 - 85 percent).Novel amino acids 9, having free carboxy groups and esterified phosphonic and phosphinic groups, could also been obtained as intermediates due to the mild conditions of the decomposition of the alkylated diastereoisomeric complexes.

ASYMMETRIC SYNTHESIS OF HETEROORGANIC ANALOGS OF NATURAL PRODUCTS. 6. (S)-α-AMINO-ω-PHOSPHONOCARBOXYLIC ACIDS

Alkylation, by ω-haloalkylphosphonates, of the Ni(II) complex of the Schiff base formed from glycine and (S)-2-N-(N1-benzylproplyl)-o-aminobenzophenone has been used for the asymmetric synthesis of (S)-2-amino-4-phosphonobutyric and (S)-2-amino-5-phosphonovaleric acids. Keywords: asymmetric synthesis; (S)-α-amino-ω-phosphonocarboxylic acids.