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
• Article Data: 9

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

• 540-69-2 ammonium formate 
• 110905-37-8 4-oxo-2-butenophosphonic acid ethyl ester 
• 120979-21-7 3-(2,5-dioxo-4-imidazolidinyl)-2-propenylphosphonic acid 
• 129084-75-9 (E)-ethyl 2-tert-butyloxycarbonylamino-5-diethylphosphono-3-pentenoate 
• 118430-50-5 N-aminocarbonyl-5-diethoxyphosphinyl-3,4-didehydro-L-norvaline 
• 118430-46-9 (2-ethoxy-4,5-didehydro-1,2-azaphosphorinane-6-yl-2-oxide)carboxylic acid 
• 121010-72-8 3-(2,5-dioxo-4-imidazolidinyl)-2-propenylphosphonic acid diethyl ester 
• 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 
• 120979-20-6 5-(3-bromo-1-propenyl)-2,4-imidazolidinedione 
• 115972-22-0 E-2-formylamino-5-diethylphosphono-3-pentenoic acid ethyl ester 
• 121010-73-9 3,4-didehydro-5-phosphono-DL-norvaline 
• 118430-40-3 5-diethoxyphosphinyl-3,4-didehydro-D-norvaline 

Downstream Products

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

Relevant articles and documents

Organophosphorus analogues and derivatives of the natural L-amino carboxylic acids and peptides. VI. A phospha(C)-peptide analogue of plumbemycin A

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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.

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.

Total synthesis, enzyme-substrate interactions and herbicidal activity of plumbemicin A and B (N-1409)

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