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Sigma-Aldrich

Phosphonoacetic acid

98%

Synonym(s):

(Carboxymethyl)phosphonic acid, 2-Phosphonoacetic acid, Fosfonoacetic acid, Phosphonacetic acid

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About This Item

Linear Formula:
(HO)2P(O)CH2CO2H
CAS Number:
4408-78-0
Molecular Weight:
140.03
EC Number:
224-558-1
MDL number:
MFCD00004311
UNSPSC Code:
12352100
PubChem Substance ID:
24857145
NACRES:
NA.22

Assay

98%

form

powder or crystals

mp

143-146 °C (lit.)

solubility

water: soluble 100 mg/mL, clear to very slightly hazy, colorless

SMILES string

OC(=O)CP(O)(O)=O

InChI

1S/C2H5O5P/c3-2(4)1-8(5,6)7/h1H2,(H,3,4)(H2,5,6,7)

InChI key

XUYJLQHKOGNDPB-UHFFFAOYSA-N

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General description

Phosphonoacetic acid inhibits specifically human cytomegalovirus DNA synthesis in virus-infected human fibroblasts. It also inhibits the synthesis of herpes simplex virus DNA in infected cells and the activity of the virus-specific DNA polymerase in vitro.

Application

Phosphonoacetic acid was used as an inhibitor of viral DNA replication, to investigate the infected cell protein 0 (bICP0) localization in infected low passage bovine cells. It was also used as a phosphorus source for microbial growth in phosphate-independent manner.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R W Honess et al.
Journal of virology, 21(2), 584-600 (1977-02-01)
Phosphonoacetic acid (PAA) inhibited the synthesis of herpes simplex virus DNA in infected cells and the activity of the virus-specific DNA polymerase in vitro. In the presence of concentrations of PAA sufficient to prevent virus growth and virus DNA synthesis
Adam D Lietzan et al.
Biochemistry, 50(45), 9708-9723 (2011-10-01)
Pyruvate carboxylase (PC) catalyzes the ATP-dependent carboxylation of pyruvate to oxaloacetate, an important anaplerotic reaction in mammalian tissues. To effect catalysis, the tethered biotin of PC must gain access to active sites in both the biotin carboxylase domain and the
Magdalena Klimek-Ochab
Folia microbiologica, 59(5), 375-380 (2014-02-27)
A psychrophilic fungal strain of Geomyces pannorum P15 was screened for its ability to utilize a range of synthetic and natural organophosphonate compounds as the sole source of phosphorus, nitrogen, or carbon. Only phosphonoacetic acid served as a phosphorus source
Vincent Li et al.
Journal of molecular biology, 400(3), 295-308 (2010-05-25)
Structure-based protein sequence alignments of family B DNA polymerases revealed a conserved motif that is formed from interacting residues between loops from the N-terminal and palm domains and between the N-terminal loop and a conserved proline residue. The importance of
A Abendroth et al.
Journal of virology, 75(10), 4878-4888 (2001-04-20)
We sought to examine the effects of varicella-zoster virus (VZV) infection on the expression of major histocompatibility complex class I (MHC I) molecules by human fibroblasts and T lymphocytes. By flow cytometry, VZV infection reduced the cell surface expression of
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