Ацетилфосфат

Description

Acetyl phosphate is a mixed anhydride of acetic and phosphoric acids, a key high-energy intermediate in the central metabolism of bacteria. Formula C2H5O5P, CAS 590-54-5, UNII 54979W5TJB, DSSTox ID DTXSID40207738. Molecular weight 140.03, exact mass 140.03. PSA characteristics: 83.8; XLogP3: -1.5. Synonyms: monoacetyl phosphate, acetic acid - anhydride with phosphoric acid, acetyl phosphate (C2H3O2(HO)2PO).

Physico-chemical characteristics

• Appearance: Solid
• Density: 1.663 g/cm3
• Boiling point: 309.5 °C at 760 mm Hg. Art.
• Flash point: 141 °C
• Refractive index: 1.459
• Collision cross section: 142.7 Å2 [M+Na]+ (method: single field calibration using Agilent tune mix); 125.44 Å2 [M+Na]+ (method: step calibration)

Substance class and biochemical role

Acetyl phosphate is a high-energy intermediate of the phosphotransacetylase-acetate kinase pathway and the main acetyl group donor in Escherichia coli. As a high-energy form of phosphate, acetyl phosphate is able to act as a donor of both acetyl and phosphoryl groups, regulating the function of proteins. Participates in the central metabolism of bacteria, and also acts as a donor of acetyl and phosphoryl groups in non-enzymatic acetylation of proteins and cellular signaling.

Mechanism of action

Acetyl phosphate is able to chemically acetylate lysine residues in proteins in vitro, and the level of acetyl phosphate correlates with the level of protein acetylation in vivo - this indicates a non-enzymatic mechanism of acetylation of cellular proteins under the influence of acetyl phosphate. Stopping the growth of a bacterial culture leads to a global increase in the level of acetylation in Escherichia coli due to the accumulation of acetyl phosphate, an intermediate metabolite of glycolysis. In Salmonella typhimurium, the regulatory protein PhoP undergoes non-enzymatic acetylation at the lysine-102 residue by acetylphosphate, which modifies its transcriptional activity and is associated with the regulation of bacterial virulence.

Scope of application

It is significant primarily as a biochemical reagent and object for studies of metabolism and regulation of bacterial virulence, as well as a model compound for studying non-enzymatic acetylation of proteins and the connection between metabolism and signal transduction. Acetyl phosphate is considered in the scientific literature as a global donor of acetyl groups in the bacterial cell - the level of its accumulation serves as a kind of metabolic sensor of the cell state, linking the availability of carbon sources with post-translational modification of regulatory proteins and, accordingly, with the virulence of pathogenic bacteria.

Effect on cellular energy metabolism

In addition to bacterial signaling, acetyl phosphate, as a product of microbial metabolism, can influence mitochondrial functions under conditions of exogenous acetylation and alkalization of the environment - this area of ​​research is relevant for understanding the interaction of the microbiota with the cells of the host organism.

Storage

There are no data on special storage conditions in the dump; as an unstable high-energy anhydride, it is stored at low temperatures, in a dry atmosphere, in containers protected from moisture.