118492-04-9

Basic information

• Product Name: 2-amino-5-phosphono-3-pentenoic acid
• Synonyms: 2-amino-5-phosphono-3-pentenoic acid;5-Phosphono-2-amino-3-pentenoic acid
• CAS NO: 118492-04-9
• Molecular Formula: C5H10 N O5 P
• Molecular Weight: 195.11
• Mol File: 118492-04-9.mol

Chemical Properties

• Boiling Point: 535.3°Cat760mmHg
• Flash Point: 277.5°C
• Appearance: /
• Density: 1.592g/cm³
• Vapor Pressure: 7E-13mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: 2-amino-5-phosphono-3-pentenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-5-phosphono-3-pentenoic acid(118492-04-9)
• EPA Substance Registry System: 2-amino-5-phosphono-3-pentenoic acid(118492-04-9)

Safety Data

• Hazardous Substances Data: 118492-04-9(Hazardous Substances Data)

Usage

Chemical Type

Phosphonate derivative of glutamic acid

Function

Selective antagonist for the N-Methyl-D-aspartate (NMDA) receptor

Applications

Used in neurobiological research to inhibit NMDA receptor activation

Biological Role

NMDA receptors play a crucial role in synaptic plasticity, learning, and memory

Research Utility

Allows researchers to study NMDA receptor functions in various biological processes

Neuroprotective Properties

Exhibits potential neuroprotective effects

Therapeutic Applications

Investigated for potential therapeutic use in conditions such as stroke and neurodegenerative diseases

Overall Significance

Valuable tool for understanding NMDA receptor roles in the central nervous system and exploring treatment options for neurological disorders

InChI:InChI=1/C5H10NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h1-2,4H,3,6H2,(H,7,8)(H2,9,10,11)/b2-1-

Upstream product

• 118430-40-3 5-diethoxyphosphinyl-3,4-didehydro-norvaline 
• 118430-50-5 N-aminocarbonyl-5-diethoxyphosphinyl-3,4-didehydro-L-norvaline 
• 118430-40-3 5-diethoxyphosphinyl-3,4-didehydro-D-norvaline 
• 118430-61-8 3,4-didehydro-5-diethoxyphosphinyl-DL-norvaline ethyl ester hydrochloride 
• 121010-81-9 DL-2-ethoxy-6-ethoxycarbonyl-1,2,3,6-tetrahydro-1,2-azaphosphorine-2-oxide 
• 121010-84-2 DL-6-ethoxycarbonyl-hydroxy-1,2,3,6-tetrahydro-1,2-azaphosphorine 2-oxide 
• 120979-21-7 3-(2,5-dioxo-4-imidazolidinyl)-2-propenylphosphonic acid 
• 120979-20-6 5-(3-bromo-1-propenyl)-2,4-imidazolidinedione 
• 121010-72-8 3-(2,5-dioxo-4-imidazolidinyl)-2-propenylphosphonic acid diethyl ester 
• 121010-73-9 3,4-didehydro-5-phosphono-DL-norvaline 
• 1449748-44-0 (S,Z)-tert-butyl 5-(dimethoxyphosphoryl)-1-hydroxypent-3-en-2-ylcarbamate 
• 1449748-43-9 (S,Z)-tert-butyl 4-(3-(dimethoxyphosphoryl)prop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1449748-42-8 (S,Z)-tert-butyl 4-(3-bromoprop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 130532-55-7 (4S)-3-N-(tert-butoxycarbonyl)-4-<3-hydroxy-(1Z)-propenyl>-2,2-dimethyl-1,3-oxazolidine 

Downstream Products

• 60978-99-6 5-phosphono-3,4-didehydro-D-norvaline 
• 76326-31-3 AP-5 

Relevant articles and documents

Synthesis and biological evaluation of potential threonine synthase inhibitors: Rhizocticin A and Plumbemycin A

Rhizocticins and Plumbemycins are natural phosphonate antibiotics produced by the bacterial strains Bacillus subtilis ATCC 6633 and Streptomyces plumbeus, respectively. Up to now, these potential threonine synthase inhibitors have only been synthesized under enzymatic catalysis. Here we report the chemical stereoselective synthesis of the non-proteinogenic (S,Z)-2-amino-5- phosphonopent-3-enoic acid [(S,Z)-APPA] and its use for the synthesis of Rhizocticin A and Plumbemycin A. In this work, (S,Z)-APPA was synthesized via the Still-Gennari olefination starting from Garner's aldehyde. The Michaelis-Arbuzov reaction was used to form the phosphorus-carbon bond. Oligopeptides were prepared using liquid phase peptide synthesis (LPPS) and were tested against selected bacteria and fungi.

Oligopeptide antibiotics

Rhizocticines of the formula STR1 in which X represents hydrogen or a hydrophobic amino acid radical and Y represents a basic amino acid radical, the C2 atoms of the amino acid radicals having the L-configuration, and protected derivatives and salts thereof. The compounds are obtained from culture broths of Bacillus subtilis or synthetically and have especially fungicidal action.

Unsaturated amino acids

The invention relates to unsaturated amino acids of the formula I STR1 in which R1 represents hydroxy or etherified hydroxy, R2 represents hydrogen, alkyl, hydroxy or etherified hydroxy, R3 represents hydrogen, alkyl, haloalkyl, hydroxyalkyl, lower alkoxyalkyl, arylalkyl, lower alkenyl, halogen or aryl, R4 represents hydrogen, alkyl or aryl, R5 represents hydrogen or alkyl, R6 represents carboxy or esterified or amidated carboxy, R7 represents amino or amino substituted by alkyl or acyl, A represents unsubstituted or alkyl-substituted α,ω-alkylene having from 1 to 3 carbon atoms or represents a bond, and B represents methylene or a bond, with the proviso that A is other than a bond when B represents a bond, and salts thereof. They can be manufactured, for example, in accordance with the Michaelis-Arbuzov reaction and can be used as pharmacologically active substances.

An Effective Synthesis of (+/-)-(E)-2-Amino-5-phosphono-3-pentenoic Acid by Palladium(II)-assisted Migration of the Double Bond

A new approach for the synthesis of (+/-)-(E)-2-amino-5-phosphono-3-pentenoic acid (E-APPA) is described.The key intermediate, (E)-5-acetoxy-3,4-dehydronorvaline derivative 8, was prepared by -sigmatropic rearrangement of allyl acetate 7 in the presence of Pd(II) catalyst.The acetoxy group in 8 was transformed into the phosphonyl group to furnish (E)-APPA in a moderate yield.

Rhizocticins - New Phosphono-Oligopeptides with Antifungal Activity

The widely used and well-known bacterial strain Bacillus subtilis ATCC 6633 was found to produce two novel, antifungal hydrophilic peptide antibiotics, L-arginyl-L-2-amino-5-phosphono-3-cis-pentenoic acid (L-Arg-L-APPA, rhizocticin A) and L-valyl-L-arginyl-L-2-amino-5-phosphono-3-cis-pentenoic acid (L-Val-L-Arg-L-APPA, rhizocticin B).Besides rhizocticin A and B, the main components, small amounts of related tripeptides were detected.Instead of the L-Val of rhizocticin B they contain L-Ile or L-Leu and are referred to as rhizocticin C and D, respectively.The C-terminal residue was identified by NMR spectroscopy as the unsaturated phosphono amino acid L-APPA, known till now only as D enantiomer.Enzymatic cleavages of rhizocticin B yielded both L-APPA and rhizocticin A.