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284270

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
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Quality Level

100

Assay

98%

form

powder or crystals

mp

143-146 °C (lit.)

solubility

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

functional group

carboxylic acid

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[1]. It also inhibits the synthesis of herpes simplex virus DNA in infected cells and the activity of the virus-specific DNA polymerase in vitro[2].

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[3]. It was also used as a phosphorus source for microbial growth in phosphate-independent manner[4].

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3645
MKCT6904
MKCT0828
MKBC4049
03598PJ

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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
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
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
Alireza Mahmoudian et al.
Comparative immunology, microbiology and infectious diseases, 35(2), 103-115 (2011-12-27)
The kinetics of expression of only a few genes of infectious laryngotracheitis virus (ILTV) have been determined, using northern blot analysis. We used quantitative reverse transcriptase PCR to examine the kinetics of expression of 74 ILTV genes in LMH cells.
E S Huang
Journal of virology, 16(6), 1560-1565 (1975-12-01)
Phosphonoacetic acid specifically inhibited human cytomegalovirus DNA synthesis in virus-infected human fibroblasts as detected by virus-specific nucleic acid hybridization. Inhibition was reversible; viral DNA synthesis resumed upon the removal of the drug. The compound partially inhibited DNA synthesis of host
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