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16051-76-6 | Phosphonic acid, P-(2-oxoethyl)-
CAS No: 16051-76-6 Catalog No: AG001RZO MDL No:MFCD24674119
Product Description
Catalog Number:
AG001RZO
Chemical Name:
Phosphonic acid, P-(2-oxoethyl)-
CAS Number:
16051-76-6
Molecular Formula:
C2H5O4P
Molecular Weight:
124.0325
MDL Number:
MFCD24674119
IUPAC Name:
2-oxoethylphosphonic acid
InChI:
InChI=1S/C2H5O4P/c3-1-2-7(4,5)6/h1H,2H2,(H2,4,5,6)
InChI Key:
YEMKIGUKNDOZEG-UHFFFAOYSA-N
SMILES:
O=CCP(=O)(O)O
Properties
Complexity:
102
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
123.993g/mol
Formal Charge:
0
Heavy Atom Count:
7
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
124.032g/mol
Monoisotopic Mass:
123.993g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
74.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.1
Literature
| Title | Journal |
|---|---|
| Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions. | Organic letters 20120615 |
| Radical-mediated enzymatic methylation: a tale of two SAMS. | Accounts of chemical research 20120417 |
| The genes and enzymes of phosphonate metabolism by bacteria, and their distribution in the marine environment. | Frontiers in microbiology 20120101 |
| Efficacy of a non-hypercalcemic vitamin-D2 derived anti-cancer agent (MT19c) and inhibition of fatty acid synthesis in an ovarian cancer xenograft model. | PloS one 20120101 |
| Angiotensin II type 2 receptor blockade inhibits fatty acid synthase production through activation of AMP-activated protein kinase in pancreatic cancer cells. | Surgery 20110801 |
| Genetic and biochemical characterization of a pathway for the degradation of 2-aminoethylphosphonate in Sinorhizobium meliloti 1021. | The Journal of biological chemistry 20110624 |
| Global analysis of the relationship between JIL-1 kinase and transcription. | PLoS genetics 20110301 |
| Regulation of histone acetylation in the hippocampus of chronically stressed rats: a potential role of sirtuins. | Neuroscience 20110203 |
| Mitochondrial biogenesis and peroxisome proliferator-activated receptor-γ coactivator-1α (PGC-1α) deacetylation by physical activity: intact adipocytokine signaling is required. | Diabetes 20110101 |
| Evolution in an oncogenic bacterial species with extreme genome plasticity: Helicobacter pylori East Asian genomes. | BMC microbiology 20110101 |
| Histone deacetylase turnover and recovery in sulforaphane-treated colon cancer cells: competing actions of 14-3-3 and Pin1 in HDAC3/SMRT corepressor complex dissociation/reassembly. | Molecular cancer 20110101 |
| Phosphonoacetate biosynthesis: in vitro detection of a novel NADP(+)-dependent phosphonoacetaldehyde-oxidizing activity in cell-extracts of the marine Roseovarius nubinhibens ISM. | Mikrobiologiia 20110101 |
| Resveratrol inhibits protein translation in hepatic cells. | PloS one 20110101 |
| Biosynthesis of rhizocticins, antifungal phosphonate oligopeptides produced by Bacillus subtilis ATCC6633. | Chemistry & biology 20100129 |
| Widespread known and novel phosphonate utilization pathways in marine bacteria revealed by functional screening and metagenomic analyses. | Environmental microbiology 20100101 |
| Carbon-dependent control of electron transfer and central carbon pathway genes for methane biosynthesis in the Archaean, Methanosarcina acetivorans strain C2A. | BMC microbiology 20100101 |
| Hydroperoxylation by hydroxyethylphosphonate dioxygenase. | Journal of the American Chemical Society 20091111 |
| cAMP pulsing of denuded mouse oocytes increases meiotic resumption via activation of AMP-activated protein kinase. | Reproduction (Cambridge, England) 20091101 |
| Concept of sustained ordering and an ATP-related mechanism of life's origin. | International journal of molecular sciences 20090501 |
| The construction of a whole-cell biosensor for phosphonoacetate, based on the LysR-like transcriptional regulator PhnR from Pseudomonas fluorescens 23F. | Microbial biotechnology 20090301 |
| A phosphorylation-acetylation switch regulates STAT1 signaling. | Genes & development 20090115 |
| Characterisation of Campylobacter jejuni genes potentially involved in phosphonate degradation. | Gut pathogens 20090101 |
| Combination effects of enalapril and losartan on lipid peroxidation in the kidneys of KK-Ay/Ta mice. | Nephron. Experimental nephrology 20090101 |
| Towards understanding phosphonoacetaldehyde hydrolase: an alternative mechanism involving proton transfer that triggers P-C bond cleavage. | Chemical communications (Cambridge, England) 20080921 |
| Biosynthesis of 2-hydroxyethylphosphonate, an unexpected intermediate common to multiple phosphonate biosynthetic pathways. | The Journal of biological chemistry 20080822 |
| The X-ray crystallographic structure and activity analysis of a Pseudomonas-specific subfamily of the HAD enzyme superfamily evidences a novel biochemical function. | Proteins 20080101 |
| AMP-activated protein kinase is involved in hormone-induced mouse oocyte meiotic maturation in vitro. | Developmental biology 20080101 |
| Effect of dietary epigallocatechin-3-gallate on cytochrome P450 2E1-dependent alcoholic liver damage: enhancement of fatty acid oxidation. | Bioscience, biotechnology, and biochemistry 20071201 |
| Unusual transformations in the biosynthesis of the antibiotic phosphinothricin tripeptide. | Nature chemical biology 20070801 |
| Reduced adipose tissue triglyceride synthesis and increased muscle fatty acid oxidation in C5L2 knockout mice. | The Journal of endocrinology 20070801 |
| Diversification of function in the haloacid dehalogenase enzyme superfamily: The role of the cap domain in hydrolytic phosphoruscarbon bond cleavage. | Bioorganic chemistry 20061201 |
| A gold standard set of mechanistically diverse enzyme superfamilies. | Genome biology 20060101 |
| Dynamic acetylation of all lysine 4-methylated histone H3 in the mouse nucleus: analysis at c-fos and c-jun. | PLoS biology 20051201 |
| The evolution of microbial phosphonate degradative pathways. | Journal of molecular evolution 20051101 |
| Isethionate as a product from taurine during nitrogen-limited growth of Klebsiella oxytoca TauN1. | Archives of microbiology 20050801 |
| A Methanocaldococcus jannaschii archaeal signature gene encodes for a 5-formaminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate synthetase. A new enzyme in purine biosynthesis. | The Journal of biological chemistry 20050325 |
| Investigation of metal ion binding in phosphonoacetaldehyde hydrolase identifies sequence markers for metal-activated enzymes of the HAD enzyme superfamily. | Biochemistry 20040504 |
| Analysis of the substrate specificity loop of the HAD superfamily cap domain. | Biochemistry 20040316 |
| X-ray crystallographic and site-directed mutagenesis analysis of the mechanism of Schiff-base formation in phosphonoacetaldehyde hydrolase catalysis. | The Journal of biological chemistry 20040305 |
| Enzymatic synthesis of radiolabeled phosphonoacetaldehyde. | Analytical biochemistry 20031115 |
| The phosphonopyruvate decarboxylase from Bacteroides fragilis. | The Journal of biological chemistry 20031017 |
| The purification and characterization of phosphonopyruvate hydrolase, a novel carbon-phosphorus bond cleavage enzyme from Variovorax sp Pal2. | The Journal of biological chemistry 20030627 |
| Kinetic evidence for a substrate-induced fit in phosphonoacetaldehyde hydrolase catalysis. | Biochemistry 20021112 |
| Degradation pathway of the phosphonate ciliatine: crystal structure of 2-aminoethylphosphonate transaminase. | Biochemistry 20021105 |
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