66508-32-5

Basic information

• Product Name: 3-(N-acetyl-N-hydroxy)aminopropylphosphonic acid
• Synonyms: 3-(N-acetyl-N-hydroxy)aminopropylphosphonic acid;3-(Acetylhydroxyamino)propylphosphonic acid;3-Phosphono 1-(N-acetylhydroxyamino)propane
• CAS NO: 66508-32-5
• Molecular Formula: C5H12NO5P
• Molecular Weight: 197.1262
• Mol File: 66508-32-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 448.9°Cat760mmHg
• Flash Point: 225.3°C
• Appearance: /
• Density: 1.492g/cm³
• Vapor Pressure: 2.6E-09mmHg at 25°C
• Refractive Index: 1.524
• PKA: 2.42±0.10(Predicted)
• CAS DataBase Reference: 3-(N-acetyl-N-hydroxy)aminopropylphosphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(N-acetyl-N-hydroxy)aminopropylphosphonic acid(66508-32-5)
• EPA Substance Registry System: 3-(N-acetyl-N-hydroxy)aminopropylphosphonic acid(66508-32-5)

Safety Data

• Hazardous Substances Data: 66508-32-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H12NO5P/c1-5(7)6(8)3-2-4-12(9,10)11/h8H,2-4H2,1H3,(H2,9,10,11)

Upstream product

• 6323-99-5 2-amino-4-phosphonobutyric acid 
• 72-89-9 acetylcoenzyme A 
• 1003599-68-5 dibenzyl {3-[acetyl(benzyloxy)amino]propyl}phosphonate 
• 66508-11-0 3-(N-hydroxyamino)-propylphosphonic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 73240-15-0 3-(N-acetyl-N-hydroxyamino)-2(R)-hydroxypropylphosphonic acid 
• 73226-73-0 3-(N-acetyl-N-hydroxyamino)-propylphosphonic acid monosodium salt 

Relevant articles and documents

Deciphering the Late Biosynthetic Steps of Antimalarial Compound FR-900098

FR-900098 is a potent chemotherapeutic agent for the treatment of malaria. Here we report the heterologous production of this compound in Escherichia coli by reconstructing the entire biosynthetic pathway using a three-plasmid system. Based on this system, whole-cell feeding assays in combination with in vitro enzymatic activity assays reveal an unusual functional role of nucleotide conjugation and lead to the complete elucidation of the previously unassigned late biosynthetic steps. These studies also suggest a biosynthetic route to a second phosphonate antibiotic, FR-33289. A thorough understanding of the FR-900098 biosynthetic pathway now opens possibilities for metabolic engineering in E. coli to increase production of the antimalarial antibiotic and combinatorial biosynthesis to generate novel derivatives of FR-900098.

Synthesis of the antimalarial drug FR900098 utilizing the nitroso-ene reaction

The antimalarial drug FR900098 was prepared from diethyl allylphosphonate involving the nitroso-ene reaction with nitrosocarbonyl methane as the key step followed by hydrogenation and dealkylation. The utilization of dibenzyl allylphosphonate as the start

STUDIES ON PHOSPHONIC ACID ANTIBIOTICS. I. STRUCTURE AND SYNTHESIS OF 3-(N-ACETYL-N-HYDROXYAMINO)PROPYLPHOSPHONIC ACID (FR-900098) AND ITS N-FORMYL ANALOGUE (FR-31564)

The structure elucidation of FR-900098 (1) isolated from a microorganism source and the syntheses of FR-900098 and its N-formyl analogue, FR-31564 (2), are described.The latter possesses a superior antimicrobial activity.