2-Amino-4-phosphonobutyric acid

Base Information

• Chemical Name: 2-Amino-4-phosphonobutyric acid
• CAS No.: 6323-99-5
• Molecular Formula: C4H10NO5P
• Molecular Weight: 183.101
• Hs Code.: 2931900090
• European Community (EC) Number: 622-387-0
• NSC Number: 354086,30079
• UNII: H8B59H10OK
• DSSTox Substance ID: DTXSID201017567
• Nikkaji Number: J327.345H
• Wikidata: Q27279766
• Pharos Ligand ID: Y2NF9U7TF5R8
• ChEMBL ID: CHEMBL285843
• Mol file: 6323-99-5.mol

Synonyms:2-amino-4-phosphonobutanoic acid;2-amino-4-phosphonobutyric acid;Abu(P);DL-2-amino-4-phosphobutanoic acid;DL-AP4;L-2-amino-4-phosphobutyric acid;L-2-amino-4-phosphonobutanoic acid;L-2-amino-4-phosphonobutyrate;L-AP4, butyric;L-APB

Chemical Property of 2-Amino-4-phosphonobutyric acid

Chemical Property:

• Melting Point: 229-231 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• Boiling Point: 491.7±55.0 °C(Predicted)
• PKA: 2.19±0.10(Predicted)
• PSA: 130.66000
• Density: 1.628±0.06 g/cm3(Predicted)
• LogP: -0.33360
• XLogP3: -5.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 183.02965942
• Heavy Atom Count: 11
• Complexity: 187

Purity/Quality:

DL-2-Amino-4-phosphonobutanoicacid(AP4) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CP(=O)(O)O)C(C(=O)O)N
• General Description: 2-Amino-4-phosphonobutyric acid (APBA) is a side chain-modified analogue used in the synthesis of 5-deazafolate and 5-deazatetrahydrofolate derivatives, demonstrating competitive inhibition against folylpolyglutamate synthetase (FPGS) and glycinamide ribonucleotide formyltransferase (GARFT). It exhibits potent inhibitory activity, with Ki values as low as 30 nM, making it a promising candidate for targeting folate metabolism and purine biosynthesis pathways.

Technology Process of 2-Amino-4-phosphonobutyric acid

There total 4 articles about 2-Amino-4-phosphonobutyric 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: 85.0%

C19H20FN2O7P*C12H23N → 2-amino-4-phosphonobutyric acid (6323-99-5) + C12H23N*C4H9FNO4P

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; acetonitrile; at 0 - 20 ℃;

DOI:10.1271/bbb.63.2248

Reference yield: 65.0%

diethyl 2-bromoethylphosphonate (5324-30-1) + methyl N-(diphenylmethylene)glycinate (81167-39-7) → 2-amino-4-phosphonobutyric acid (6323-99-5)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; In acetonitrile; for 24h; Heating;

Reference yield:

2-Amino-4-(dimethoxy-phosphoryl)-butyric acid methyl ester (86554-31-6) → 2-Amino-4-phosphono-butyric acid (6323-99-5,20263-07-4,23052-81-5,78739-01-2) + 2-Amino-4-phosphono-butyric acid (6323-99-5,20263-07-4,23052-81-5,78739-01-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

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

upstream raw materials:

diethyl 2-bromoethylphosphonate

methyl N-(diphenylmethylene)glycinate

2-Amino-4-(dimethoxy-phosphoryl)-butyric acid methyl ester

Downstream raw materials:

2-N-benzoylamino-4-phosphonobutyric acid

2-(N-benzyloxycarbonylamino)-4-phosphonobutanoic acid

tetraethyl ethylenebis(phosphonate)

amino-2 diethylphosphono-4 butyrate d'ethyle

Refernces

Side chain modified 5-deazafolate and 5-deazatetrahydrofolate analogues as mammalian folylpolyglutamate synthetase and glycinamide ribonucleotide formyltransferase inhibitors: Synthesis and in vitro biological evaluation

10.1021/jm00087a012

This research aimed to synthesize and evaluate a series of 5-deazafolate and 5-deazatetrahydrofolate analogues as potential inhibitors of folylpolyglutamate synthetase (FPGS) and glycinamide ribonucleotide formyltransferase (GARFT), enzymes involved in folate metabolism and purine biosynthesis, respectively. The researchers synthesized analogues by replacing the glutamic acid side chain with homocysteic acid (HCysA), 2-amino-4-phosphonobutanoic acid (APBA), and ornithine (Om). The compounds were tested for their inhibitory effects on mouse liver FPGS and GARFT. The results showed that the analogues with HCysA and monoethyl APBA side chains were less active as FPGS inhibitors, while Orn and APBA analogues exhibited competitive inhibition kinetics and were more potent, with Ki values as low as 30 nM.