Acetylphosphate

• CAS: 590-54-5
• Catalog Number: ACM590545
• Category: Main Products
• Molecular Weight: 140.03
• Molecular Formula: C₂H₅O₅P
• Synonyms: Acetyl-phosphorsaeure; Acetylphosphic acid; monoacetyl phosphate; acetyldihydrogen-phosphat; UVW; acetylphosphoric acid; acetyl-P; Dihydroxyphosphinyl Acetate; phosphono acetate; Acetic acid,monoanhydride with phosphoric acid; acetylphosphate
• IUPAC Name: phosphonoacetate
• Canonical SMILES: CC(=O)OP(=O)(O)O
• InChI Key: LIPOUNRJVLNBCD-UHFFFAOYSA-N
• Boiling Point: 309.5ºC at 760 mmHg
• Flash Point: 141ºC
• Density: 1.663 g/cm³
• Exact Mass: 139.98700

Case Study

Acetylphosphate is a key player in lysine acetylation in Escherichia coli

Weinert, Brian T., et al. Molecular cell 51.2 (2013): 265-272.

Lysine acetylation is a frequent post-translational modification in bacteria; however, its origin and regulation are poorly understood. Using the model bacterium Escherichia coli (E. coli), we found that most acetylation occurs at low levels and accumulates in growth-arrested cells in a manner that is dependent on the formation of acetyl phosphate (AcP) through glycolysis. Mutant cells that are unable to produce AcP have significantly reduced acetylation levels, while mutant cells that are unable to convert AcP to acetate have significantly increased acetylation levels. We found that AcP can chemically acetylate lysine residues in vitro and that AcP levels correlate with acetylation levels in vivo, suggesting that AcP can acetylate proteins in cells in a non-enzymatic manner. These results reveal a key role for AcP in bacterial acetylation and suggest that most acetylation in E. coli occurs at low levels and is dynamically affected by metabolism and cell proliferation in a global, uniform manner.
Purified Adk was mixed with freshly prepared acetyl phosphate at 37°C for 3 h. Protein lysates (10 mg in 1 ml) from SILAC-labeled BL21 cells were supplemented with 10 mM nicotinamide to inhibit CobB deacetylase activity and incubated with AcP for 1 h at 37°C. Acetyl phosphate levels were determined essentially as described by converting acetyl phosphate to ATP using commercially available acetate kinase.

Acetylphosphate acts as a global signal during biofilm formation

Wolfe, Alan J., et al. Molecular microbiology 48.4 (2003): 977-988.

DNA macroarray analysis was used to identify genes that respond to the status of the intracellular acetyl phosphate (acP) pool. Genes whose expression correlated negatively with the ability to synthesize acP (i.e., negative regulators) primarily play a role in flagellar biosynthesis. In contrast, genes whose expression correlated positively with the ability to synthesize acP included those involved in type 1 pili assembly, colanic acid (capsule) biosynthesis, and certain stress effectors. Therefore, it was tested whether cells with altered acP metabolism were able to build normal biofilms and were not. Both cells defective in acP production and cells defective in acP degradation could form biofilms, but these biofilms exhibited features that differed significantly from each other and from those formed by their wild-type parents.
The results of DNA macroarray experiments designed to identify acetyl phosphate (acP)-responsive genes indicate that the status of the acP pool regulates the expression of cellular components required for normal biofilm development. It is envisioned that acP regulates the initial steps of biofilm formation by coupling the expression of flagella, pili, and colanic acid to the nutritional status of the culture, presumably through several two-component response regulators. Wild-type planktonic cells undergoing the transition from exponential growth to stationary phase are expected to have a small pool of acP, assemble some flagella and some pili, and synthesize small amounts of colanic acid. However, once these wild-type cells come into contact with a suitable surface or with each other, the subsequent local depletion of nutrients and oxygen is predicted to result in elevated intracellular acP levels.

Acetylphosphate and activation of two-component response regulators

McCleary, William R., and Jeffry B. Stock.Journal of Biological Chemistry 269.50 (1994): 31567-31572.

Several bacterial response regulators (CheY, NRv, PhoB, and OmpR) are phosphorylated in vitro when incubated with acetyl phosphate. In the presence of high levels of acetyl phosphate and Me, CheY reaches steady-state phosphorylation in less than 30 seconds; NRv and PhoB reach steady-state more slowly, at 1.5 minutes and >15 minutes, respectively. A simple method was developed to measure acetyl phosphate levels in E. coli grown in defined media. Acetyl phosphate is elevated in cells grown on pyruvate, glucose, and glucuronic acid, and is lower in cells grown on fructose, glycerol, and fumarate. The effects of altering intracellular acetyl phosphate levels on chemotaxis and osmotic responses were also investigated.
The wild-type strain was used in all experiments. PE101 is a deletion strain constructed by transducing a ligated TnlO (zej-223::Tnl) from BW16463 into YMC10. RP437 is the wild type chemotactic strain and PE103 is its A(pta acM his& hisP) derivative. Strains containing the A(pta acM his& hzsP mutations were tested for growth on fluoroacetate plates and the ability to synthesize acetyl phosphate or pyruvate while growing. Measurement of acetyl phosphate- Cells were grown in modified MOPS minimal medium containing limiting phosphate (0.2 mM). During exponential growth in the early stationary phase, 0.30 ml of cells were transferred from the culture flask to a 1.5 ml microcentrifuge tube. The cells were incubated at room temperature for 30 minutes to allow phosphate equilibration. To the 0.20 ml labeled cells, 20 μl of 11 formic acid was added and mixed immediately and allowed to stand on ice for 30 minutes. To this extract, 20 μl of phosphate precipitation solution was added and mixed. The phosphate precipitation solution consisted of five parts 400 mM sodium tungstate, four parts 500 mM tetraethylammonium hydrochloride, and one part 500 mM procaine.

Acetyl phosphate as a substrate for origin of life

Whicher, Alexandra, et al. Origins of Life and Evolution of Biospheres 48 (2018): 159-179.

Metabolism is initiated by thioester formation and ATP phosphorylation of acetyl CoA. Prebiotic equivalents such as methyl thioacetate and acetyl phosphate have been proposed to catalyze similar reactions at the origin of life, but their propensity for hydrolysis challenges this view. It was demonstrated that acetyl phosphate (AcP) can be synthesized from thioacetate (but not methyl thioacetate) in water within minutes under ambient conditions. AcP remains stable for hours, depending on temperature, pH, and cation content, giving it an ideal balance between stability and reactivity. AcP can phosphorylate ribose precursors to ribose 5-phosphate and adenosine to adenosine monophosphate with modest yields (about 2%) in water and over a range of pH. AcP can also phosphorylate ADP to ATP over hours at 50 °C in water. However, AcP does not promote polymerization of glycine or AMP. The amino group of glycine is preferentially acetylated by AcP, especially at alkaline pH, hindering polypeptide formation. AMP forms small stacks of up to 7 monomers, but these monomers do not polymerize in the presence of AcP in aqueous solution.
Solutions of D-ribose (0.3 M) and acetyl phosphate (0.3 M) were prepared, and aqueous solutions containing MgCl2, CaCl2, or boric acid (0.15 M) were added when applicable. Experiments were performed at pH 7, 9, and 11, 20°C and 50°C, and samples were taken at 2, 30, 60, 120, 300 min, and 1, 2, and 5 days. The mobile phase solvents were (A) water/0.1% formic acid (FA) and (B) acetonitrile/0.1% FA, with a flow rate of 200 μL/min. The optimal solvent gradient started at 98% A and gradually decreased to 5% A at 18 min; after holding at 5% A for 1 min, the gradient reached the initial condition (98% A) in the last 5.5 min. Derivatization with 3-amino-9-ethylcarbazole and a solid phase extraction (SPE) protocol were used followed by 0.22 μm microfiltration using retention times and primary and MSMS fragmentation patterns of standards; quantification was performed using calibration curves for each experimental condition (pH and ion concentration).

Custom Q&A

What is the molecular formula of acetylphosphate?

The molecular formula of acetylphosphate is C2H5O5P.

What are the synonyms of acetylphosphate?

The synonyms of acetylphosphate are acetyl phosphate, 590-54-5, phosphono acetate, and acetyl dihydrogen phosphate.

What is the molecular weight of acetylphosphate?

The molecular weight of acetylphosphate is 140.03 g/mol.

What is the role of acetylphosphate in Escherichia coli?

Acetylphosphate has a role as an Escherichia coli metabolite.

What is the conjugate acid of acetylphosphate?

The conjugate acid of acetylphosphate is an acetyl phosphate(1-).

Where is acetylphosphate found in nature?

Acetylphosphate is found in Euglena gracilis, Saccharomyces cerevisiae, and Drosophila melanogaster.

What is the IUPAC name of acetylphosphate?

The IUPAC name of acetylphosphate is phosphono acetate.

What is the InChIKey of acetylphosphate?

The InChIKey of acetylphosphate is LIPOUNRJVLNBCD-UHFFFAOYSA-N.

What is the CAS number of acetylphosphate?

The CAS number of acetylphosphate is 590-54-5.

What is the physical description of acetylphosphate?

Acetylphosphate is a solid.