2-Amino-3-phosphonopropionic acid

Base Information

• Chemical Name: 2-Amino-3-phosphonopropionic acid
• CAS No.: 5652-28-8
• Molecular Formula: C3H8 N O5 P
• Molecular Weight: 169.07
• Hs Code.: 2931499090
• European Community (EC) Number: 633-843-3
• NSC Number: 133887,30078
• UNII: 0H89G8110O
• DSSTox Substance ID: DTXSID40863590
• Nikkaji Number: J81.069J
• Wikidata: Q27236782
• Metabolomics Workbench ID: 37223
• ChEMBL ID: CHEMBL88621
• Mol file: 5652-28-8.mol

Synonyms:2-amino-3-phosphono-propionic acid;2-amino-3-phosphonopropionate;2-amino-3-phosphonopropionic acid;2-amino-3-phosphonopropionic acid, (DL)-isomer;2-amino-3-phosphonopropionic acid, sodium salt;2-amino-3-phosphopropionic acid;2-amino-3-PHOSPROP;2-AP3;3-phosphono-L-alanine;3-phosphonoalanine;alanine, 3-phosphono-;L-AP3;phosphonoalanine

Chemical Property of 2-Amino-3-phosphonopropionic acid

Chemical Property:

• Boiling Point: 481.6°Cat760mmHg
• PKA: 1.22±0.10(Predicted)
• Flash Point: 245.1°C
• PSA: 130.66000
• Density: 1.763g/cm³
• LogP: -0.72370
• XLogP3: -5.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 169.01400935
• Heavy Atom Count: 10
• Complexity: 174

Purity/Quality:

99%min ^*data from raw suppliers

DL-2-Amino-3-phosphonopropionicAcid(AP3) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(C(=O)O)N)P(=O)(O)O
• Description: Metabotropic glutamate receptors (mGluR1-8) are G protein-coupled receptors that function to modulate brain excitatory signaling via presynaptic, postsynaptic, and glial mechanisms. DL-AP3 is a competitive mGluR1 antagonist that demonstrates a Ki value of 298 μM and an IC50 value of 1mM for rat mGluR1α when challenged with glutamate. DL-AP3 can antagonize excitatory amino acid-induced phosphoinositide hydrolysis, induce Ca2+ mobilization in rat hippocampal slices, and inhibit phosphoserine phosphatase in rat brain cortex. At concentrations from 10-300 μM DL-AP3 has been used to characterize the role of mGluR in long-term potentiation in the hippocampus in a model of learning and memory, the release of glutamate in Parkinson’s disease, and the increased activity of mGluR implicated in fragile X syndrome.

Technology Process of 2-Amino-3-phosphonopropionic acid

There total 2 articles about 2-Amino-3-phosphonopropionic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-((S)-1-Phenyl-ethylamino)-3-phosphono-propionic acid (86554-28-1,86554-34-9) → 2-Amino-3-phosphono-propionic acid (5652-28-8,20263-06-3,23052-80-4,128241-72-5) + 2-Amino-3-phosphono-propionic acid (5652-28-8,20263-06-3,23052-80-4,128241-72-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; at 100 ℃; for 10h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(01)91895-2

Reference yield:

2-((S)-1-Phenyl-ethylamino)-3-phosphono-propionic acid (86554-28-1,86554-34-9) → 2-Amino-3-phosphono-propionic acid (5652-28-8,20263-06-3,23052-80-4,128241-72-5) + 2-Amino-3-phosphono-propionic acid (5652-28-8,20263-06-3,23052-80-4,128241-72-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; at 100 ℃; for 10h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(01)91895-2

Reference yield: 65.0%

DL-2-amino-3-phosphonopropionic acid (5652-28-8) + benzyl alcohol (100-51-6,185532-71-2) → benzyl DL-2-amino-3-phosphonopropanoate (113811-52-2)

Guidance literature:

With thionyl chloride; for 18h; Ambient temperature;

DOI:10.1021/jm00402a012

upstream raw materials:

2-((S)-1-Phenyl-ethylamino)-3-phosphono-propionic acid

Downstream raw materials:

benzyl DL-2-amino-3-phosphonopropanoate

3‐phosphopyruvate

Refernces