Home Bromides 1113-59-3
1113-59-3,MFCD00149107
Catalog No.:AA0035SA

1113-59-3 | Bromopyruvic acid

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1mg
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5g
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10g
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25g
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500g
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0035SA
Chemical Name:
Bromopyruvic acid
CAS Number:
1113-59-3
Molecular Formula:
C3H3BrO3
Molecular Weight:
166.9581
MDL Number:
MFCD00149107
SMILES:
OC(=O)C(=O)CBr
Properties
Properties
 
BP:
223.4°C at 760 mmHg  
Form:
Solid  
MP:
77-82 °C  
Refractive Index:
1.4650 (estimate)  
Solubility:
water: soluble1g/10 mL, clear, colorless  
Storage:
Inert atmosphere;-20 ℃;  

Computed Properties
 
Complexity:
98.4  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
7  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  
XLogP3:
0.5  

Literature

Title: Antitumor and chemosensitizing action of 3-bromopyruvate: Implication of deregulated metabolism.

Journal: Chemico-biological interactions 20170525

Title: Mechanisms underlying 3-bromopyruvate-induced cell death in colon cancer.

Journal: Journal of bioenergetics and biomembranes 20150101

Title: Regulation of death induction and chemosensitizing action of 3-bromopyruvate in myeloid leukemia cells: energy depletion, oxidative stress, and protein kinase activity modulation.

Journal: The Journal of pharmacology and experimental therapeutics 20140201

Title: MCT1-mediated transport of a toxic molecule is an effective strategy for targeting glycolytic tumors.

Journal: Nature genetics 20130101

Title: D-Amino acid oxidase-induced oxidative stress, 3-bromopyruvate and citrate inhibit angiogenesis, exhibiting potent anticancer effects.

Journal: Journal of bioenergetics and biomembranes 20121001

Title: Glutamine deprivation enhances antitumor activity of 3-bromopyruvate through the stabilization of monocarboxylate transporter-1.

Journal: Cancer research 20120901

Title: Glycolysis inhibitors as a potential therapeutic option to treat aggressive neuroblastoma expressing GLUT1.

Journal: Journal of pediatric surgery 20120701

Title: Prognostic significance of glucose transporter-1 (GLUT1) gene expression in rectal cancer after preoperative chemoradiotherapy.

Journal: Surgery today 20120501

Title: 3-Bromopyruvate inhibits calcium uptake by sarcoplasmic reticulum vesicles but not SERCA ATP hydrolysis activity.

Journal: The international journal of biochemistry & cell biology 20120501

Title: Casiopeina II-gly and bromo-pyruvate inhibition of tumor hexokinase, glycolysis, and oxidative phosphorylation.

Journal: Archives of toxicology 20120501

Title: Aerosolized 3-bromopyruvate inhibits lung tumorigenesis without causing liver toxicity.

Journal: Cancer prevention research (Philadelphia, Pa.) 20120501

Title: Mefloquine interferes with glycolysis in schistosomula of Schistosoma mansoni via inhibition of enolase.

Journal: Parasitology 20120401

Title: Mitochondrial genome-knockout cells demonstrate a dual mechanism of action for the electron transport complex I inhibitor mycothiazole.

Journal: Marine drugs 20120401

Title: Science to practice: what do molecular biologic studies in rodent models add to our understanding of interventional oncologic procedures including percutaneous ablation by using glyceraldehyde-3-phosphate dehydrogenase antagonists?

Journal: Radiology 20120301

Title: Human hepatocellular carcinoma in a mouse model: assessment of tumor response to percutaneous ablation by using glyceraldehyde-3-phosphate dehydrogenase antagonists.

Journal: Radiology 20120301

Title: Effect of glucose availability on glucose transport in bovine mammary epithelial cells.

Journal: Animal : an international journal of animal bioscience 20120301

Title: PPARγ contributes to PKM2 and HK2 expression in fatty liver.

Journal: Nature communications 20120214

Title: Rab25 increases cellular ATP and glycogen stores protecting cancer cells from bioenergetic stress.

Journal: EMBO molecular medicine 20120201

Title: Up-regulation of hexokinaseII in myeloma cells: targeting myeloma cells with 3-bromopyruvate.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: 3-Bromopyruvate: targets and outcomes.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: 3-Bromopyruvate antagonizes effects of lactate and pyruvate, synergizes with citrate and exerts novel anti-glioma effects.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: Bromopyruvate mediates autophagy and cardiolipin degradation to monolyso-cardiolipin in GL15 glioblastoma cells.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: Flow cytometric evaluation of the effects of 3-bromopyruvate (3BP) and dichloracetate (DCA) on THP-1 cells: a multiparameter analysis.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: Effect of the antitumoral alkylating agent 3-bromopyruvate on mitochondrial respiration: role of mitochondrially bound hexokinase.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: Experimental results using 3-bromopyruvate in mesothelioma: in vitro and in vivo studies.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: A translational study 'case report' on the small molecule 'energy blocker' 3-bromopyruvate (3BP) as a potent anticancer agent: from bench side to bedside.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: Targeting aerobic glycolysis: 3-bromopyruvate as a promising anticancer drug.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: Enhancement of hexokinase II inhibitor-induced apoptosis in hepatocellular carcinoma cells via augmenting ER stress and anti-angiogenesis by protein disulfide isomerase inhibition.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: Butyrate activates the monocarboxylate transporter MCT4 expression in breast cancer cells and enhances the antitumor activity of 3-bromopyruvate.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: Over-expression of GAPDH in human colorectal carcinoma as a preferred target of 3-bromopyruvate propyl ester.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: Transport and cytotoxicity of the anticancer drug 3-bromopyruvate in the yeast Saccharomyces cerevisiae.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: 3-Bromopyruvate (3BP) a fast acting, promising, powerful, specific, and effective 'small molecule' anti-cancer agent taken from labside to bedside: introduction to a special issue.

Journal: Journal of bioenergetics and biomembranes 20120201

Title: D-amino acid oxidase gene therapy sensitizes glioma cells to the antiglycolytic effect of 3-bromopyruvate.

Journal: Cancer gene therapy 20120101

Title: Intracellular ATP levels are a pivotal determinant of chemoresistance in colon cancer cells.

Journal: Cancer research 20120101

Title: Systemic administration of 3-bromopyruvate in treating disseminated aggressive lymphoma.

Journal: Translational research : the journal of laboratory and clinical medicine 20120101

Title: Cancer metabolism: current perspectives and future directions.

Journal: Cell death & disease 20120101

Title: Clotrimazole preferentially inhibits human breast cancer cell proliferation, viability and glycolysis.

Journal: PloS one 20120101

Title: Thyrocyte-specific inactivation of p53 and Pten results in anaplastic thyroid carcinomas faithfully recapitulating human tumors.

Journal: Oncotarget 20111201

Title: MondoA senses non-glucose sugars: regulation of thioredoxin-interacting protein (TXNIP) and the hexose transport curb.

Journal: The Journal of biological chemistry 20111104

Title: Mitochondrial dysfunction and effect of antiglycolytic bromopyruvic acid in GL15 glioblastoma cells.

Journal: Journal of bioenergetics and biomembranes 20111001

Title: Role of SLC5A8, a plasma membrane transporter and a tumor suppressor, in the antitumor activity of dichloroacetate.

Journal: Oncogene 20110922

Title: Metabolic oxidative stress elicited by the copper(II) complex [Cu(isaepy)2] triggers apoptosis in SH-SY5Y cells through the induction of the AMP-activated protein kinase/p38MAPK/p53 signalling axis: evidence for a combined use with 3-bromopyruvate in neuroblastoma treatment.

Journal: The Biochemical journal 20110801

Title: Inhibition of hypoxia-inducible carbonic anhydrase-IX enhances hexokinase II inhibitor-induced hepatocellular carcinoma cell apoptosis.

Journal: Acta pharmacologica Sinica 20110701

Title: Metabolism and brain cancer.

Journal: Clinics (Sao Paulo, Brazil) 20110601

Title: Novel intraarterial therapy for liver cancer using ethylbromopyruvate dissolved in an iodized oil.

Journal: Academic radiology 20110401

Title: Assessment of tumoricidal efficacy and response to treatment with 18F-FDG PET/CT after intraarterial infusion with the antiglycolytic agent 3-bromopyruvate in the VX2 model of liver tumor.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20110201

Title: Cellular ATP synthesis mediated by type III sodium-dependent phosphate transporter Pit-1 is critical to chondrogenesis.

Journal: The Journal of biological chemistry 20110128

Title: Inhibition of hexokinase leads to neuroprotection against excitotoxicity in organotypic hippocampal slice culture.

Journal: Journal of neuroscience research 20110101

Title: The bioenergetic signature of isogenic colon cancer cells predicts the cell death response to treatment with 3-bromopyruvate, iodoacetate or 5-fluorouracil.

Journal: Journal of translational medicine 20110101

Title: The dynamics of glutathione species and ophthalmate concentrations in plasma from the VX2 rabbit model of secondary liver tumors.

Journal: HPB surgery : a world journal of hepatic, pancreatic and biliary surgery 20110101

Title: Stereocomplexes Formed From Select Oligomers of Polymer d-lactic Acid (PDLA) and l-lactate May Inhibit Growth of Cancer Cells and Help Diagnose Aggressive Cancers-Applications of the Warburg Effect.

Journal: Perspectives in medicinal chemistry 20110101

Title: Mitochondrial approaches to protect against cardiac ischemia and reperfusion injury.

Journal: Frontiers in physiology 20110101

Title: The metabolic advantage of tumor cells.

Journal: Molecular cancer 20110101

Title: Antioxidant properties of aminoethylcysteine ketimine decarboxylated dimer: a review.

Journal: International journal of molecular sciences 20110101

Title: Differential utilization of ketone bodies by neurons and glioma cell lines: a rationale for ketogenic diet as experimental glioma therapy.

Journal: BMC cancer 20110101

Title: Anticancer targets in the glycolytic metabolism of tumors: a comprehensive review.

Journal: Frontiers in pharmacology 20110101

Title: Efficient elimination of cancer cells by deoxyglucose-ABT-263/737 combination therapy.

Journal: PloS one 20110101

Title: Mitochondrial NAD+-dependent malic enzyme from Anopheles stephensi: a possible novel target for malaria mosquito control.

Journal: Malaria journal 20110101

Title: Systematic exploration of synergistic drug pairs.

Journal: Molecular systems biology 20110101

Title: Glycolysis inhibition inactivates ABC transporters to restore drug sensitivity in malignant cells.

Journal: PloS one 20110101

Title: Lactate produced by glycogenolysis in astrocytes regulates memory processing.

Journal: PloS one 20110101

Title: 3-bromopyruvate: a new targeted antiglycolytic agent and a promise for cancer therapy.

Journal: Current pharmaceutical biotechnology 20100801

Title: Interventional oncology: new options for interstitial treatments and intravascular approaches: targeting tumor metabolism via a loco-regional approach: a new therapy against liver cancer.

Journal: Journal of hepato-biliary-pancreatic sciences 20100701

Title: Interleukin-7 mediates glucose utilization in lymphocytes through transcriptional regulation of the hexokinase II gene.

Journal: American journal of physiology. Cell physiology 20100601

Title: 3-Bromopyruvate induces necrotic cell death in sensitive melanoma cell lines.

Journal: Biochemical and biophysical research communications 20100528

Title: The pyruvic acid analog 3-bromopyruvate interferes with the tetrazolium reagent MTS in the evaluation of cytotoxicity.

Journal: Assay and drug development technologies 20100401

Title: Glycolytic enzyme inhibitors affect pancreatic cancer survival by modulating its signaling and energetics.

Journal: Anticancer research 20100301

Title: 3-Bromopyruvate induces endoplasmic reticulum stress, overcomes autophagy and causes apoptosis in human HCC cell lines.

Journal: Anticancer research 20100301

Title: Fully automated continuous flow synthesis of highly functionalized imidazo[1,2-a] heterocycles.

Journal: Organic letters 20100205

Title: Cancer as a metabolic disease.

Journal: Nutrition & metabolism 20100101

Title: Quantitative proteomics identification of phosphoglycerate mutase 1 as a novel therapeutic target in hepatocellular carcinoma.

Journal: Molecular cancer 20100101

Title: Analyzing the regulation of metabolic pathways in human breast cancer.

Journal: BMC medical genomics 20100101

Title: Role of the mitochondrion in programmed necrosis.

Journal: Frontiers in physiology 20100101

Title: Glyceraldehyde-3-phosphate dehydrogenase (GAPDH) is pyruvylated during 3-bromopyruvate mediated cancer cell death.

Journal: Anticancer research 20091201

Title: Targets of 3-bromopyruvate, a new, energy depleting, anticancer agent.

Journal: Medicinal chemistry (Shariqah (United Arab Emirates)) 20091101

Title: Transport by SLC5A8 with subsequent inhibition of histone deacetylase 1 (HDAC1) and HDAC3 underlies the antitumor activity of 3-bromopyruvate.

Journal: Cancer 20091015

Title: Metabolic control analysis in a cellular model of elevated MAO-B: relevance to Parkinson's disease.

Journal: Neurotoxicity research 20091001

Title: Glucose deprivation contributes to the development of KRAS pathway mutations in tumor cells.

Journal: Science (New York, N.Y.) 20090918

Title: A one-pot synthesis of functionalized thiazoles from acid chlorides, secondary amines, ethyl bromopyruvate, and ammonium thiocyanate.

Journal: Molecular diversity 20090801

Title: Inhibitive effect of 3-bromopyruvic acid on human breast cancer MCF-7 cells involves cell cycle arrest and apoptotic induction.

Journal: Chinese medical journal 20090720

Title: Role of mitochondria-associated hexokinase II in cancer cell death induced by 3-bromopyruvate.

Journal: Biochimica et biophysica acta 20090501

Title: Mitochondria and energetic depression in cell pathophysiology.

Journal: International journal of molecular sciences 20090501

Title: Specificity of the anti-glycolytic activity of 3-bromopyruvate confirmed by FDG uptake in a rat model of breast cancer.

Journal: Investigational new drugs 20090401

Title: Hexokinase inhibitor screening based on adenosine 5'-diphosphate determination by electrophoretically mediated microanalysis.

Journal: Electrophoresis 20090401

Title: Novel therapy for malignant pleural mesothelioma based on anti-energetic effect: an experimental study using 3-Bromopyruvate on nude mice.

Journal: Anticancer research 20090401

Title: Inhibition of glycolysis modulates prednisolone resistance in acute lymphoblastic leukemia cells.

Journal: Blood 20090226

Title: Inhibition of energy-producing pathways of HepG2 cells by 3-bromopyruvate.

Journal: The Biochemical journal 20090201

Title: Hexokinase-2 bound to mitochondria: cancer's stygian link to the 'Warburg Effect' and a pivotal target for effective therapy.

Journal: Seminars in cancer biology 20090201

Title: Senescence induction; a possible cancer therapy.

Journal: Molecular cancer 20090101

Title: The antitumor effect and hepatotoxicity of a hexokinase II inhibitor 3-bromopyruvate: in vivo investigation of intraarterial administration in a rabbit VX2 hepatoma model.

Journal: Korean journal of radiology 20090101

Title: Role of reactive oxygen species-mediated mitochondrial dysregulation in 3-bromopyruvate induced cell death in hepatoma cells : ROS-mediated cell death by 3-BrPA.

Journal: Journal of bioenergetics and biomembranes 20081201

Title: Non-invasive MRI tumor imaging and synergistic anticancer effect of HSP90 inhibitor and glycolysis inhibitor in RIP1-Tag2 transgenic pancreatic tumor model.

Journal: Cancer chemotherapy and pharmacology 20081101

Title: Targeting of VX2 rabbit liver tumor by selective delivery of 3-bromopyruvate: a biodistribution and survival study.

Journal: The Journal of pharmacology and experimental therapeutics 20081001

Title: Hamster sperm capacitation: role of pyruvate dehydrogenase A and dihydrolipoamide dehydrogenase.

Journal: Biology of reproduction 20080801

Title: Strategies for molecular imaging dementia and neurodegenerative diseases.

Journal: Neuropsychiatric disease and treatment 20080601

Title: 3-Bromopyruvate as inhibitor of tumour cell energy metabolism and chemopotentiator of platinum drugs.

Journal: Molecular oncology 20080601

Title: Synergistic antipancreatic tumor effect by simultaneously targeting hypoxic cancer cells with HSP90 inhibitor and glycolysis inhibitor.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080315

Title: Revealing targeted therapy for human cancer by gene module maps.

Journal: Cancer research 20080115

Title: A novel strategy involved in [corrected] anti-oxidative defense: the conversion of NADH into NADPH by a metabolic network.

Journal: PloS one 20080101

Title: Development of a new orthotopic animal model of metastatic liver cancer in the rabbit VX2 model: effect on metastases after partial hepatectomy, intra-arterial treatment with 3-bromopyruvate and chemoembolization.

Journal: Clinical & experimental metastasis 20080101

Title: Systems biology approach to identification of biomarkers for metastatic progression in cancer.

Journal: BMC bioinformatics 20080101

Title: Cytometric assessment of DNA damage by exogenous and endogenous oxidants reports aging-related processes.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20071101

Title: Apoptosis-inducing antitumor efficacy of hexokinase II inhibitor in hepatocellular carcinoma.

Journal: Molecular cancer therapeutics 20070901

Title: Warburg, me and Hexokinase 2: Multiple discoveries of key molecular events underlying one of cancers' most common phenotypes, the 'Warburg Effect', i.e., elevated glycolysis in the presence of oxygen.

Journal: Journal of bioenergetics and biomembranes 20070601

Title: [Expression of hexokinase-II gene in human colon cancer cells and the therapeutic significance of inhibition thereof].

Journal: Zhonghua yi xue za zhi 20070417

Title: The cancer cell's 'power plants' as promising therapeutic targets: an overview.

Journal: Journal of bioenergetics and biomembranes 20070201

Title: Local toxicity of hepatic arterial infusion of hexokinase II inhibitor, 3-bromopyruvate: In vivo investigation in normal rabbit model.

Journal: Academic radiology 20070101

Title: Intraarterial therapy with a new potent inhibitor of tumor metabolism (3-bromopyruvate): identification of therapeutic dose and method of injection in an animal model of liver cancer.

Journal: Journal of vascular and interventional radiology : JVIR 20070101

Title: FDG-PET for evaluating the antitumor effect of intraarterial 3-bromopyruvate administration in a rabbit VX2 liver tumor model.

Journal: Korean journal of radiology 20070101

Title: The oncoprotein H-RasV12 increases mitochondrial metabolism.

Journal: Molecular cancer 20070101

Title: The role of glucose metabolism and glucose-associated signalling in cancer.

Journal: Perspectives in medicinal chemistry 20070101

Title: Hepatic intra-arterial injection of 3-bromopyruvate in rabbit VX2 tumor.

Journal: Acta radiologica (Stockholm, Sweden : 1987) 20061201

Title: Colony-stimulating factor-1 requires PI3-kinase-mediated metabolism for proliferation and survival in myeloid cells.

Journal: Cell death and differentiation 20061101

Title: Inactivation of H+-vacuolar ATPase by the energy blocker 3-bromopyruvate, a new antitumour agent.

Journal: Life sciences 20061019

Title: Hexokinase II: cancer's double-edged sword acting as both facilitator and gatekeeper of malignancy when bound to mitochondria.

Journal: Oncogene 20060807

Title: Synthesis of functionalized 5-imino-2,5-dihydro-furans through the reaction of isocyanides with activated acetylenes in the presence of ethyl bromopyruvate.

Journal: Molecular diversity 20060801

Title: Hypoxia stimulates proliferation of human hepatoma cells through the induction of hexokinase II expression.

Journal: Journal of hepatology 20050301

Title: Inhibition of glycolysis in cancer cells: a novel strategy to overcome drug resistance associated with mitochondrial respiratory defect and hypoxia.

Journal: Cancer research 20050115

Title: Targeting energy metabolism in brain cancer: review and hypothesis.

Journal: Nutrition & metabolism 20050101

Title: Advanced cancers: eradication in all cases using 3-bromopyruvate therapy to deplete ATP.

Journal: Biochemical and biophysical research communications 20041105

Title: Flux to acetate and lactate excretions in industrial fermentations: physiological and biochemical implications.

Journal: Journal of industrial microbiology & biotechnology 20040801

Title: Carbonic anhydrase in mammalian vascular smooth muscle.

Journal: The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society 20040801

Title: Recently elucidated energy catabolism pathways provide opportunities for novel treatments in hepatocellular carcinoma.

Journal: Expert review of anticancer therapy 20040601

Title: Crystal structure of 2-methylisocitrate lyase (PrpB) from Escherichia coli and modelling of its ligand bound active centre.

Journal: Journal of molecular biology 20030502

Title: Glycolytic ATP production regulates muscarinic cation currents in guinea-pig ileum.

Journal: Journal of smooth muscle research = Nihon Heikatsukin Gakkai kikanshi 20030401

Title: A new approach to therapy for hepatocellular carcinoma?

Journal: Hepatology (Baltimore, Md.) 20030201

Title: Biochemical and structural studies of malate synthase from Mycobacterium tuberculosis.

Journal: The Journal of biological chemistry 20030117

Title: Energy blocker to treat liver cancer.

Journal: Drug discovery today 20020915

Title: 3-Bromopyruvate kills cancer cells in animals.

Journal: The Lancet. Oncology 20020901

Title: Novel therapy for liver cancer: direct intraarterial injection of a potent inhibitor of ATP production.

Journal: Cancer research 20020715

Title: Lack of antifertility properties of novel halogenated glycolytic inhibitors and the urinary excretion and metabolism of 1,6-dichloro-1,6-dideoxy-D-fructofuranose in the male rat.

Journal: International journal of andrology 20020601

Title: An absolute requirement of fructose 1,6-bisphosphate for the Lactobacillus casei L-lactate dehydrogenase activity induced by a single amino acid substitution.

Journal: Protein engineering 20020101

Title: Investigation of red blood cell carbonic anhydrase, glucose 6-phosphate dehydrogenase, hexokinase enzyme activities, and zinc concentration in patients with hyperthyroid diseases.

Journal: Endocrine research 20020101

Title: Glucose catabolism in the rabbit VX2 tumor model for liver cancer: characterization and targeting hexokinase.

Journal: Cancer letters 20011108

Title: Modification of human erythrocyte pyruvate kinase by an active site-directed reagent: bromopyruvate.

Journal: Journal of enzyme inhibition 20011101

Title: 2-Methylisocitrate lyases from the bacterium Escherichia coli and the filamentous fungus Aspergillus nidulans: characterization and comparison of both enzymes.

Journal: European journal of biochemistry 20010601

Title: Alkylation of isocitrate lyase from Escherichia coli by 3-bromopyruvate.

Journal: Archives of biochemistry and biophysics 19900501

Title: Chemical modifications of Serratia marcescens anthranilate synthase component I.

Journal: The Journal of biological chemistry 19811010

Title: Equilibrium substrate binding studies of the malic enzyme of pigeon liver. Equivalence of nucleotide sites and anticooperativity associated with the binding of L-malate to the enzyme-manganese(II)-reduced nicotinamide adenine dinucleotide phosphate ternary complex.

Journal: Biochemistry 19800304

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Tags:1113-59-3 Molecular Formula|1113-59-3 MDL|1113-59-3 SMILES|1113-59-3 Bromopyruvic acid |Organic_Building_Blocks