23052-81-5

Usage

Uses

Used in Pharmaceutical Industry:
L-AP4 is used as a mGluR-4/6 receptor agonist for modulating excitatory synaptic transmission in the brain. Its agonistic activity at Group III mGluRs helps in suppressing glutamate release, which can be beneficial in treating various neurological disorders associated with excessive glutamate activity.
Used in Neuroscience Research:
L-AP4 is used as a research tool to study the role of mGluRs in synaptic transmission and neuronal function. Its selective agonistic activity at Group III mGluRs allows researchers to investigate the specific mechanisms and pathways involved in these processes.
Used in Neurological Disorder Treatment:
L-AP4 is used as a potential therapeutic agent for neurological disorders characterized by hyperexcitability and excessive glutamate release, such as epilepsy, neuropathic pain, and certain neurodegenerative diseases. Its ability to suppress glutamate release makes it a promising candidate for the development of novel treatments for these conditions.

Biological Activity

Selective group III metabotropic glutamate receptor agonist. Synaptic depressant. Agonist at the quisqualate-sensitized AP6 site in hippocampus. Also available as part of the Group III mGlu Receptor Tocriset? and Mixed mGlu Receptor Tocriset? .

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-/m0/s1

Upstream product

• 141894-89-5 S(+)-2-amino-4-diethoxyphosphonobutanoic acid 
• 127593-79-7 ethyl 2-((1R,2R,5R)-2-hydroxypinan-3-imino)glycinate 
• 682-30-4 Diethyl vinylphosphonate 
• 86554-31-6 2-Amino-4-(dimethoxy-phosphoryl)-butyric acid methyl ester 

Relevant academic research and scientific papers

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.

L-(+)-2-amino-4-thiophosphonobutyric acid (L-thioAP4), a new potent agonist of group III metabotropic glutamate receptors: Increased distal acidity affords enhanced potency

L-2-Amino-4-phosphonobutyric acid (L-AP4), L-2-amino-4-thiophosphonobutyric acid (L-thioAP4), and L-2-amino-4-(hydroxy)phosphinylbutyric acid (desmethylphosphinothricin, DMPT) were synthesized from protected vinylglycine. They were tested as agonists at g

Highly Efficient and Divergent Construction of Chiral γ-Phosphono-α-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated C(sp3)-H Bonds

Chiral γ-phosphono-α-amino acids play a crucial role in inhibitors of natural enzymes, as well as agonists and antagonists of metabotropic glutamate receptors. In this paper, an efficient and general protocol for the construction of chiral γ-phosphono-α-amino acids via Pd-catalyzed AQ-directed C(sp3)-H alkylation of α-amino acid derivatives is developed. The reaction shows reactivity between methylene C(sp3)-H bonds with phosphonated alkyl iodides with high yields, enantioselectivity, and diastereomeric ratios, which enables access to a wide range of challenging and important γ-phosphono-α-amino acids in large scale. Meanwhile, δ-phosphono-α-amino acid and δ-phosphono-propionic acid derivatives can also be successfully obtained. The derivatization reaction in the synthesis of l-AP4 and l-phosphinothricin highlight the applicability of this method.

OPTICALLY-ACTIVE 2-AMINO-PHOSPHONOALKANE ACID, OPTICALLY-ACTIVE 2-AMINOPHOSPHONOALKANE ACID SALT, AND HYDRATES OF THESE

A novel compound has pharmacological activities comparable to those of Nahlsgen and is storable excellently stably. The compound can be produced by a method according to the present invention for producing an optically active 2-amino-phosphonoalkanoic acid salt. In the method, a starting material DL-2-amino-phosphonoalkanoic acid represented by Formula (1) or a hydrate thereof is reacted with an optically active basic compound other than an optically active lysine, to give a diastereomeric salt mixture including a first salt (including a hydrate salt) between a D-2-amino-phosphonoalkanoic acid represented by Formula (1-1) and the optically active basic compound, and a second salt (including a hydrate salt) between an L-2-amino-phosphonoalkanoic acid represented by Formula (1-2) and the optically active basic compound. The diastereomeric salt mixture is fractionally crystallized to isolate one of the first and second diastereomeric salts.

A general approach to enantiomeric γ-aminophosphonic acids using chiral sulfinimine methodology

A new approach to asymmetric synthesis of γ-aminophosphonic acids is described. It involves the diastereoselective addition of various carbon and phosphorus nucleophiles to enantiopure (+)-(S)-N-[(3-diethoxyphosphoryl) propylidene]-p-toluenesulfinamide an

THIOPHOSPHI(O)NIC ACID DERIVATIVES AND THEIR THERAPEUTICAL APPLICATIONS

The invention relates to thiophosphi(o)nic acid derivatives having formula (I) wherein. M is a [C(R3,R4)]n1-C(E,COOR1,N(H,Z)) group, or an optionally substituted Ar—CH(COOR1,N(H,Z)) group (Ar designating an aryl

The invention of radical reactions. Part 39. The reaction of white phosphorus with carbon-centered radicals. An improved procedure for the synthesis of phosphonic acids and further mechanistic insights

White phosphorus in tetrahydrofuran under argon reacts in a long radical chain reaction with carbon radicals derived from Barton PTOC esters. The reaction is initiated by traces of oxygen and strongly inhibited by TEMPO. From the duration of the induction period the chain length can be measured as approximately one million. Each P4 molecule can add up to two carbon radicals. Oxidation of the adducts provides a convenient synthesis of phosphonic acids in high yield. With H2O2 at 0°C oxidation to the appropriate phosphinic acids is fast. For sensitive natural products the further transformation to phosphonic acids is best carried out at room temperature with an excess of SO2. In this way even linoleic acid can be convened to the corresponding phosphonic acid in good yield without any attack on the skipped diene unit. TEMPO is also remarkable for its stabilization of white phosphorus in solution when exposed to oxygen. Likewise an ordinary phosphine, like tributyl phosphine, is also stabilized by small amounts of TEMPO.

Lipase-catalyzed enantioselective acylation of prochiral 2-(ω)-phosphono)alkyl-1,3-propanediols: Application to the enantioselective synthesis of ω-phosphono-α-amino acids

Lipase PS catalyzed acetylation of prochiral 2-(ω-phosphono)alkyl-1,3-propanediols 1a-c was found to proceed with high enantioselectivity. The applications of phosphonic chirons 2a-c thus obtained were illustrated by the stereocontrolled synthesis of ω-phosphono-α-amino acids such as L-AP-3, L-AP-4, and N-Boc-L-F2Pab(OEt)2-OH.

A novel asymmetric synthesis of S-(+)-2-amino-4-phosphonobutanoic acid

A novel asymmetric synthetic route to S(+)-2-amino-4-phosphonobutanoic acid through the cyclic condensation of ethyl-4-diethyoxyphosphonyl-2-oxo-butanoate with L-erythro-(+)-1,2-diphenyl-2-hydroxyethylamine, followed by reduction and hydrolysis is describ

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.