85178-62-7

Usage

Uses

Used in Pharmaceutical Development:
[(3S)-3-amino-3-carboxypropyl](hydroxy)oxophosphonium is used as a potential target for the development of novel antibiotics and herbicides. Its importance in the pyruvate phosphate dikinase reaction makes it a strategic point of intervention to disrupt carbon metabolism in pathogenic bacteria and agricultural pests, thereby controlling infectious diseases and managing agricultural threats.
Used in Metabolic Research:
In the field of metabolic research, [(3S)-3-amino-3-carboxypropyl](hydroxy)oxophosphonium is utilized for further investigation into the role of ACP in carbon metabolism. Studying its function and interaction with PPDK can lead to a deeper understanding of metabolic pathways, which is essential for developing new strategies to combat various diseases and pests.
Used in Agricultural Science:
[(3S)-3-amino-3-carboxypropyl](hydroxy)oxophosphonium is used as a basis for developing new herbicides targeting the carbon metabolism of agricultural pests. By inhibiting the function of ACP, these herbicides can effectively control pest populations, reducing the impact on crops and improving agricultural productivity.
Used in Microbiology:
In microbiology, [(3S)-3-amino-3-carboxypropyl](hydroxy)oxophosphonium is employed in the study of pathogenic bacteria's carbon metabolism. Understanding how ACP contributes to bacterial survival and growth can inform the development of new antibiotics that specifically target these metabolic processes, enhancing the effectiveness of treatments against bacterial infections.

Upstream product

• 89131-53-3 Ethyl 3,3-dicarbethoxy-3-acetamidopropylphosphonous acid 
• 89131-41-9 O-ethyl-vinylphosphonite 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 864682-69-9 (S)-2-benzyloxycarbonylamino-4-hydroxyphosphinoyl-butyric acid methyl ester 
• 3705-42-8 Cbz-(L)-Glu-OBn 
• 55327-87-2 2-acetamidomalonic acid 

Downstream Products

• 35597-44-5 L-phosphinothricin 
• 135093-66-2 N-acetyldemethylphosphinothricin 

Relevant academic research and scientific papers

Convenient syntheses of phosphinic analogues of γ-aminobutyric- and glutamic acids

Three-steps, one-pot synthesis of 2-amino-4-(hydroxyphosphinyl)butyric acid from dibutyl ester of vinylphosphinic acid was carried out with an overall yield of 66%. 3-Aminopropylphosphinic acid was prepared from allylamine in three steps with an overall y

Spectroscopic characterization and mechanistic investigation of P-methyl transfer by a radical SAM enzyme from the marine bacterium Shewanella denitrificans OS217

Natural products containing carbon-phosphorus bonds elicit important bioactivity in many organisms. l-Phosphinothricin contains the only known naturally-occurring carbon-phosphorus-carbon bond linkage. In actinomycetes, the cobalamin-dependent radical S-adenosyl-l-methionine (SAM) methyltransferase PhpK catalyzes the formation of the second C-P bond to generate the complete C-P-C linkage in phosphinothricin. Here we use electron paramagnetic resonance and nuclear magnetic resonance spectroscopies to characterize and demonstrate the activity of a cobalamin-dependent radical SAM methyltransferase denoted SD-1168 from Shewanella denitrificans OS217, a marine bacterium that has not been reported to synthesize phosphinothricin. Recombinant, refolded, and reconstituted SD-1168 binds a four-iron, four-sulfur cluster that interacts with SAM and cobalamin. In the presence of SAM, a reductant, and methylcobalamin, SD-1168 surprisingly catalyzes the P-methylation of N-acetyl-demethylphosphinothricin and demethylphosphinothricin to produce N-acetyl-phosphinothricin and phosphinothricin, respectively. In addition, this enzyme is active in the absence of methylcobalamin if the strong reductant titanium (III) citrate and hydroxocobalamin are provided. When incubated with [methyl-13C] cobalamin and titanium citrate, both [methyl-13C] and unlabeled N-acetylphosphinothricin are produced. Our results suggest that SD-1168 catalyzes P-methylation using radical SAM-dependent chemistry with cobalamin as a coenzyme. In light of recent genomic information, the discovery of this P-methyltransferase suggests that S. denitrificans produces a phosphinate natural product.

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

1-Aminoalkylphosphonous Acids. Part 1. Isosteres of the Protein Amino Acids

The synthesis of 1-aminoalkylphosphonous acids, isosteres of the protein amino acids, by addition of hypophosphorous acid to diphenylmethylimines is described.These analogues of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrosine, tryptophan, serine, threonine, methionine, cysteine, cystine, glutamic acid, lysine, ornithine, arginine, and proline have been prepared and the analogues of alanine, valine, leucine, phenylalanine, and methionine resolved.The alanine, valine and methionine analogues have interesting antimicrobial activity and the alanine analogue has plant growth inhibiting properties.Oxidation of the appropriate 1-aminoalkylphosphonous acids gave the 1-aminoalkylphosphonic acid analogues of (+/-)-alanine, (-)-alanine, (+/-)-valine, (-)-valine, (+/-)-serine, (+/-)-threonine, (+/-)-lysine, (-)-leucine, and (+/-)-ornithine.

SYNTHESIS AND PROPERTIES OF PHOSPHINOTRICIN DERIVATIVES

The synthesis and properties of phosphinotricin derivatives which have different alkyl groups attached to phosphorus or bear a substituent on the nitrogen are described and their biological activities discussed.

ORGANIC PHOSPHORUS COMPOUNDS 77 SYNTHESIS AND PROPERTIES OF PHOSPHINOTHRICIN HOMOLOGS AND ANALOGS

The synthesis, chemical, and spectral properties of (3-amino-3-hydroxycarbonyl-propyl)phosphonous acid (2), bis(3-amino-3-hydroxycarbonylpropyl)phosphinic acid (5), (2-amino-2-hydroxycarbonylethyl)-methylphosphinic acid (6), (1-amino-2-hydroxycarbonylethy