Home Other Building Blocks 2-METHYLCITRIC ACID

2-METHYLCITRIC ACID

CAS No.:
6061-96-7
Catalog Number:
AG00EBUP
Molecular Formula:
Molecular Weight:
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Purity
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Product Description
Catalog Number:
AG00EBUP
Chemical Name:
2-METHYLCITRIC ACID
CAS Number:
6061-96-7
MDL Number:
MFCD01074482
IUPAC Name:
2-hydroxybutane-1,2,3-tricarboxylic acid
InChI:
InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)
InChI Key:
YNOXCRMFGMSKIJ-UHFFFAOYSA-N
Properties
Complexity:
271  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
206.043g/mol
Formal Charge:
0
Heavy Atom Count:
14  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
206.15g/mol
Monoisotopic Mass:
206.043g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
132A^2
Undefined Atom Stereocenter Count:
2  
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.4  
Literature
Title Journal
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Molecular characterization of PrpR, the transcriptional activator of propionate catabolism in Corynebacterium glutamicum. Journal of biotechnology 20120531
Living-donor liver transplantation for propionic acidemia. Pediatric transplantation 20120501
Genome-wide transcriptional profiling of appressorium development by the rice blast fungus Magnaporthe oryzae. PLoS pathogens 20120201
Saturation diving alters folate status and biomarkers of DNA damage and repair. PloS one 20120101
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Complete genome sequence, lifestyle, and multi-drug resistance of the human pathogen Corynebacterium resistens DSM 45100 isolated from blood samples of a leukemia patient. BMC genomics 20120101
Variable carbon catabolism among Salmonella enterica serovar Typhi isolates. PloS one 20120101
A novel role of the PrpR as a transcription factor involved in the regulation of methylcitrate pathway in Mycobacterium tuberculosis. PloS one 20120101
Complete genome sequence of Allochromatium vinosum DSM 180(T). Standards in genomic sciences 20111231
Vitamin B12, cognition, and brain MRI measures: a cross-sectional examination. Neurology 20110927
Comparative and functional genomics of Rhodococcus opacus PD630 for biofuels development. PLoS genetics 20110901
Differential producibility analysis (DPA) of transcriptomic data with metabolic networks: deconstructing the metabolic response of M. tuberculosis. PLoS computational biology 20110601
Transcriptome analysis of Neisseria meningitidis in human whole blood and mutagenesis studies identify virulence factors involved in blood survival. PLoS pathogens 20110501
Adeno-associated virus serotype 8 gene transfer rescues a neonatal lethal murine model of propionic acidemia. Human gene therapy 20110401
Crystal structure of Salmonella typhimurium 2-methylcitrate synthase: Insights on domain movement and substrate specificity. Journal of structural biology 20110401
Development and implementation of an electronic interface for complex clinical laboratory instruments without a vendor-provided data transfer interface. Journal of pathology informatics 20110101
New developments in the treatment of hyperammonemia: emerging use of carglumic acid. International journal of general medicine 20110101
Genome-scale reconstruction and in silico analysis of the Ralstonia eutropha H16 for polyhydroxyalkanoate synthesis, lithoautotrophic growth, and 2-methyl citric acid production. BMC systems biology 20110101
Proteomic analysis reveals that iron availability alters the metabolic status of the pathogenic fungus Paracoccidioides brasiliensis. PloS one 20110101
Serum methionine metabolites are risk factors for metastatic prostate cancer progression. PloS one 20110101
Comparative genomics of the pathogenic ciliate Ichthyophthirius multifiliis, its free-living relatives and a host species provide insights into adoption of a parasitic lifestyle and prospects for disease control. Genome biology 20110101
Death of the TonB Shuttle Hypothesis. Frontiers in microbiology 20110101
Comparative genomics of Helicobacter pylori and the human-derived Helicobacter bizzozeronii CIII-1 strain reveal the molecular basis of the zoonotic nature of non-pylori gastric Helicobacter infections in humans. BMC genomics 20110101
Determination of total homocysteine, methylmalonic acid, and 2-methylcitric acid in dried blood spots by tandem mass spectrometry. Clinical chemistry 20101101
Investigations on the microbial catabolism of the organic sulfur compounds TDP and DTDP in Ralstonia eutropha H16 employing DNA microarrays. Applied microbiology and biotechnology 20101101
An automated phenotype-driven approach (GeneForce) for refining metabolic and regulatory models. PLoS computational biology 20101001
Drug off-target effects predicted using structural analysis in the context of a metabolic network model. PLoS computational biology 20100901
Vitamin B12 deficiency in African American and white octogenarians and centenarians in Georgia. The journal of nutrition, health & aging 20100501
Preliminary X-ray crystallographic analysis of 2-methylcitrate synthase from Salmonella typhimurium. Acta crystallographica. Section F, Structural biology and crystallization communications 20100401
The sex pheromone of the wasp spider Argiope bruennichi. Angewandte Chemie (International ed. in English) 20100308
Functioning in situ: gene expression in Methylotenera mobilis in its native environment as assessed through transcriptomics. The ISME journal 20100301
Volatile profiling reveals intracellular metabolic changes in Aspergillus parasiticus: veA regulates branched chain amino acid and ethanol metabolism. BMC biochemistry 20100101
Quinone-dependent D-lactate dehydrogenase Dld (Cg1027) is essential for growth of Corynebacterium glutamicum on D-lactate. BMC microbiology 20100101
Methylcitrate cycle activation during adaptation of Fusarium solani and Fusarium verticillioides to propionyl-CoA-generating carbon sources. Microbiology (Reading, England) 20091201
Evidence for catabolic pathway of propionate metabolism in CNS: expression pattern of methylmalonyl-CoA mutase and propionyl-CoA carboxylase alpha-subunit in developing and adult rat brain. Neuroscience 20091201
Adaptation to beta-myrcene catabolism in Pseudomonas sp. M1: an expression proteomics analysis. Proteomics 20091101
Roles of the glyoxylate and methylcitrate cycles in sexual development and virulence in the cereal pathogen Gibberella zeae. Eukaryotic cell 20090801
Microbial inactivation properties of a new antimicrobial/antithrombotic catheter lock solution (citrate/methylene blue/parabens). Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20090601
Disruption of the 2-methylcitric acid cycle and evaluation of poly-3-hydroxybutyrate-co-3-hydroxyvalerate biosynthesis suggest alternate catabolic pathways of propionate in Burkholderia sacchari. Canadian journal of microbiology 20090601
Diverse protein regulations on PHA formation in Ralstonia eutropha on short chain organic acids. International journal of biological sciences 20090101
Visualizing post genomics data-sets on customized pathway maps by ProMeTra-aeration-dependent gene expression and metabolism of Corynebacterium glutamicum as an example. BMC systems biology 20090101
Functional genomics of pH homeostasis in Corynebacterium glutamicum revealed novel links between pH response, oxidative stress, iron homeostasis and methionine synthesis. BMC genomics 20090101
Prenatal diagnosis of propionic acidemia by measuring methylcitric acid in dried amniotic fluid on filter paper using GC/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080715
Newborn screening for methylmalonic acidurias--optimization by statistical parameter combination. Journal of inherited metabolic disease 20080601
Construction and use of new cloning vectors for the rapid isolation of recombinant proteins from Escherichia coli. Plasmid 20080501
Prenatal diagnosis of methylmalonic aciduria by analysis of organic acids and total homocysteine in amniotic fluid. Chinese medical journal 20080205
Co-ordinated regulation of gluconate catabolism and glucose uptake in Corynebacterium glutamicum by two functionally equivalent transcriptional regulators, GntR1 and GntR2. Molecular microbiology 20080101
Investigation of central carbon metabolism and the 2-methylcitrate cycle in Corynebacterium glutamicum by metabolic profiling using gas chromatography-mass spectrometry. Journal of biotechnology 20070715
The three-dimensional crystal structure of the PrpF protein of Shewanella oneidensis complexed with trans-aconitate: insights into its biological function. Protein science : a publication of the Protein Society 20070701
Characterisation of the 1H and 13C NMR spectra of methylcitric acid. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20070601
1H NMR spectra of methylcitric acid in urine. Journal of inherited metabolic disease 20070401
Metabolic phenotype of methylmalonic acidemia in mice and humans: the role of skeletal muscle. BMC medical genetics 20070101
Metabolic engineering of strains of Ralstonia eutropha and Pseudomonas putida for biotechnological production of 2-methylcitric acid. Metabolic engineering 20061101
Metabolic changes associated with hyperammonemia in patients with propionic acidemia. Molecular genetics and metabolism 20060601
Identification of a transposable genomic island of Paracoccus pantotrophus DSM 11072 by its transposition to a novel entrapment vector pMMB2. Microbiology (Reading, England) 20060401
Two newborns with nutritional vitamin B12 deficiency: challenges in newborn screening for vitamin B12 deficiency. Haematologica 20051201
Novel and established markers of cobalamin deficiency: complementary or exclusive diagnostic strategies. Seminars in vascular medicine 20050501
Biotin deficiency in an infant fed with amino acid formula. The Journal of dermatology 20050401
2-Methylcitrate-dependent activation of the propionate catabolic operon (prpBCDE) of Salmonella enterica by the PrpR protein. Microbiology (Reading, England) 20041101
Potential cardiovascular risk factors in chronic kidney disease: AGEs, total homocysteine and metabolites, and the C-reactive protein. Kidney international 20040701
Metabolic markers of cobalamin deficiency and cognitive function in normal older adults. Journal of the American Geriatrics Society 20040101
Metabolic carbon fluxes and biosynthesis of polyhydroxyalkanoates in Ralstonia eutropha on short chain fatty acids. Biotechnology progress 20040101
A knock-out mouse model for methylmalonic aciduria resulting in neonatal lethality. The Journal of biological chemistry 20031226
Development of a Corynebacterium glutamicum DNA microarray and validation by genome-wide expression profiling during growth with propionate as carbon source. Journal of biotechnology 20031219
Methylmalonic acid, a biochemical hallmark of methylmalonic acidurias but no inhibitor of mitochondrial respiratory chain. The Journal of biological chemistry 20031128
Crystal structure of Salmonella typhimurium 2-methylisocitrate lyase (PrpB) and its complex with pyruvate and Mg(2+). Biochemical and biophysical research communications 20031107
Serum levels of total homocysteine, homocysteine metabolites and of advanced glycation end-products (AGEs) in patients after renal transplantation. Clinical nephrology 20030201
Cloning, expression, purification and preliminary X-ray crystallographic studies of 2-methylisocitrate lyase from Salmonella typhimurium. Acta crystallographica. Section D, Biological crystallography 20021201
Rapid and sensitive method for prenatal diagnosis of propionic acidemia using stable isotope dilution gas chromatography-mass spectrometry and urease pretreatment. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020825
Validated capillary gas chromatographic-mass spectrometric assay to determine 2-methylcitric acid I and II levels in human serum by using a pulsed splitless injection procedure. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20020805
Is low-dose oral cobalamin enough to normalize cobalamin function in older people? Journal of the American Geriatrics Society 20020801
Neurodegeneration in methylmalonic aciduria involves inhibition of complex II and the tricarboxylic acid cycle, and synergistically acting excitotoxicity. The Journal of biological chemistry 20020426
Screening for cobalamin deficiency in geriatric outpatients: prevalence and influence of synthetic cobalamin intake. Journal of the American Geriatrics Society 20020401
Pentaerythritol propoxylate: a new crystallization agent and cryoprotectant induces crystal growth of 2-methylcitrate dehydratase. Acta crystallographica. Section D, Biological crystallography 20020201
Rhodothermus marinus: a thermophilic bacterium producing dimeric and hexameric citrate synthase isoenzymes. Extremophiles : life under extreme conditions 20020201
AcnC of Escherichia coli is a 2-methylcitrate dehydratase (PrpD) that can use citrate and isocitrate as substrates. Microbiology (Reading, England) 20020101
The methylcitric acid pathway in Ralstonia eutropha: new genes identified involved in propionate metabolism. Microbiology (Reading, England) 20010801
Studies of propionate toxicity in Salmonella enterica identify 2-methylcitrate as a potent inhibitor of cell growth. The Journal of biological chemistry 20010601
In vitro conversion of propionate to pyruvate by Salmonella enterica enzymes: 2-methylcitrate dehydratase (PrpD) and aconitase Enzymes catalyze the conversion of 2-methylcitrate to 2-methylisocitrate. Biochemistry 20010417
Homocyst(e)ine metabolism in hemodialysis patients treated with vitamins B6, B12 and folate. Research in experimental medicine. Zeitschrift fur die gesamte experimentelle Medizin einschliesslich experimenteller Chirurgie 20010301
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Properties