Аргининефосфомицин

Substance identification

Arginine fosfomycin is a conjugate of phosphonic acid of the fosfomycin series with the amino acid arginine. English name argininefosfomycin, CAS 70518-66-0, chemical formula C9H21N4O6P. Classification section - phosphines (organophosphorus compounds).

Synonyms

• Arginine fosfomycin
• Arginine fosfomycin, (D)-isomer
• L-arginine, (2R-cis)-(3-methyloxiranyl)phosphonate (11)

Physico-chemical characteristics

• Molecular weight: 312.260001
• Exact weight: 312.12
• DSSTox ID: DTXSID80220789
• PSA specification: 198

Connection class and purpose

The compound belongs to the phosphonate antibiotics of the fosfomycin series - epoxypropylphosphonic acid, known for inhibiting the enzyme MurA (UDP-N-acetylglucosamine-enolpyruvyltransferase), which catalyzes the first stage of peptidoglycan biosynthesis of the bacterial cell wall. The addition of arginine to phosphonic acid forms a conjugate salt that increases the solubility and bioavailability of the active phosphonate moiety compared to the free acid. The high value of the polar surface (PSA 198) reflects the pronounced hydrophilicity of the molecule due to the guanidine group of arginine and the phosphonate residue.

Scope of application

It is used in research practice as a reference compound in the study of structure-activity relationships in the series of fosfomycin and its salt forms, as well as in the development of analytical methods for the determination of phosphonate antibiotics and their metabolites using HPLC-MS methods.

Fosfomycin series of salts

Fosfomycin as an active substance is used in medicine in the form of sodium salt (for parenteral administration) and trometamol salt (for oral administration for urinary tract infections); amino acid conjugates, including the arginine form, are being studied as alternative salt forms with different solubility and stability profiles. The presence of arginine in the structure of the molecule distinguishes the compound from classical inorganic salts of fosfomycin and makes it a convenient object for comparative physicochemical studies in a series of salt forms of the same phosphonic acid.

Storage and handling

Store in an airtight container in a cool, dry place, protected from light and moisture. The substance is hygroscopic due to the ionic nature of the arginine salt, so the package must be tightly closed after opening. When working with dry powder, avoid dust, use personal protective equipment - gloves and goggles, work in a fume hood when pouring and weighing. Working solutions are prepared immediately before use, since aqueous solutions of phosphonates are subject to slow hydrolysis of the epoxy ring during long-term storage. Transportation and storage of the reagent as a laboratory standard do not require special conditions for dangerous goods, however, the general rules for handling organophosphorus reagents - separate storage from acids and oxidizing agents - remain valid.

Analytical value

The molecule combines phosphonate and amino acid fragments, which makes it a convenient model compound for testing ion-pair and ion-exclusion chromatography methods in the analysis of polar antibiotics that are poorly retained on reverse-phase sorbents.