200,000+ products from a single source!
sales@angenechem.com
Home > Other Building Blocks > 526-99-8
526-99-8 | (2R,3S,4R,5S);-2,3,4,5-Tetrahydroxyhexanedioic acid
CAS No: 526-99-8 Catalog No: AG003S6M MDL No:MFCD00004239
Product Description
Catalog Number:
AG003S6M
Chemical Name:
(2R,3S,4R,5S);-2,3,4,5-Tetrahydroxyhexanedioic acid
CAS Number:
526-99-8
Molecular Formula:
C6H10O8
Molecular Weight:
210.1388
MDL Number:
MFCD00004239
IUPAC Name:
(2S,3R,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid
InChI:
InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2+,3+,4-
InChI Key:
DSLZVSRJTYRBFB-DUHBMQHGSA-N
SMILES:
O[C@H]([C@H](C(=O)O)O)[C@H]([C@@H](C(=O)O)O)O
EC Number:
208-404-0
UNII:
E149J5OTIF
Properties
Complexity:
202
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
0
Exact Mass:
210.038g/mol
Formal Charge:
0
Heavy Atom Count:
14
Hydrogen Bond Acceptor Count:
8
Hydrogen Bond Donor Count:
6
Isotope Atom Count:
0
Molecular Weight:
210.138g/mol
Monoisotopic Mass:
210.038g/mol
Rotatable Bond Count:
5
Topological Polar Surface Area:
156A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.5
Literature
| Title | Journal |
|---|---|
| Changing patterns of anemia management in US hemodialysis patients. | The American journal of medicine 20120901 |
| Lysyl hydroxylase 3-mediated glucosylation in type I collagen: molecular loci and biological significance. | The Journal of biological chemistry 20120629 |
| Detection of myocardial ischemia-reperfusion injury using a fluorescent near-infrared zinc(II)-dipicolylamine probe and 99mTc glucarate. | Molecular imaging 20120601 |
| Characterization of a novel Agrobacterium tumefaciens galactarolactone cycloisomerase enzyme for direct conversion of D-galactarolactone to 3-deoxy-2-keto-L-threo-hexarate. | The Journal of biological chemistry 20120518 |
| Computer simulations of osmotic ultrafiltration and small-solute transport in peritoneal dialysis: a spatially distributed approach. | American journal of physiology. Renal physiology 20120515 |
| Enhancing liver mitochondrial fatty acid oxidation capacity in obese mice improves insulin sensitivity independently of hepatic steatosis. | Journal of hepatology 20120301 |
| Modulation of Pseudomonas aeruginosa lipopolysaccharide-induced lung inflammation by chronic iron overload in rat. | FEMS immunology and medical microbiology 20120301 |
| Protective role of D-saccharic acid-1,4-lactone in alloxan induced oxidative stress in the spleen tissue of diabetic rats is mediated by suppressing mitochondria dependent apoptotic pathway. | Free radical research 20120301 |
| Modifications in the nitric acid oxidation of D-glucose. | Carbohydrate research 20120301 |
| Clinical case reports raise doubts about the therapeutic equivalence of an iron sucrose similar preparation compared with iron sucrose originator. | Current medical research and opinion 20120201 |
| Disruption of the chemokine-like receptor-1 (CMKLR1) gene is associated with reduced adiposity and glucose intolerance. | Endocrinology 20120201 |
| Iron sucrose promotes endothelial injury and dysfunction and monocyte adhesion/infiltration. | American journal of nephrology 20120201 |
| Comparison of oxidative stress and inflammation induced by different intravenous iron sucrose similar preparations in a rat model. | Inflammation & allergy drug targets 20120201 |
| Effective components screening and anti-myocardial infarction mechanism study of the Chinese medicine NSLF6 based on 'system to system' mode. | Journal of translational medicine 20120101 |
| A bio-catalytic approach to aliphatic ketones. | Scientific reports 20120101 |
| Glucuronidated quercetin lowers blood pressure in spontaneously hypertensive rats via deconjugation. | PloS one 20120101 |
| Differential effects of subtype-specific nicotinic acetylcholine receptor agonists on early and late hippocampal LTP. | European journal of pharmacology 20111205 |
| D-saccharic acid-1,4-lactone ameliorates alloxan-induced diabetes mellitus and oxidative stress in rats through inhibiting pancreatic β-cells from apoptosis via mitochondrial dependent pathway. | Toxicology and applied pharmacology 20111201 |
| High-value chemicals obtained from selective photo-oxidation of glucose in the presence of nanostructured titanium photocatalysts. | Bioresource technology 20111201 |
| Vascular deconjugation of quercetin glucuronide: the flavonoid paradox revealed? | Molecular nutrition & food research 20111201 |
| Characterization of D-glucaric acid using NMR, X-ray crystal structure, and MM3 molecular modeling analyses. | Carbohydrate research 20111129 |
| Combination of erythritol and fructose increases gastrointestinal symptoms in healthy adults. | Nutrition research (New York, N.Y.) 20111101 |
| Do two intravenous iron sucrose preparations have the same efficacy? | Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20111001 |
| Modulation of biomarkers related to tumor initiation and promotion in mouse skin by a natural β-glucuronidase inhibitor and its precursors. | Oncology reports 20110901 |
| Metabolic fingerprinting of Leontopodium species (Asteraceae) by means of ¹H NMR and HPLC-ESI-MS. | Phytochemistry 20110801 |
| New insights on the mechanism of oxidation of D-galacturonic acid by hypervalent chromium. | Dalton transactions (Cambridge, England : 2003) 20110714 |
| Carbohydrate-based polyesters made from bicyclic acetalized galactaric acid. | Biomacromolecules 20110711 |
| Structure-activity examination of poly(glycoamidoguanidine)s: glycopolycations containing guanidine units for nucleic acid delivery. | Biomacromolecules 20110613 |
| In vitro study of the antioxidative properties of the glucose derivatives against oxidation of plasma components. | Journal of physiology and biochemistry 20110601 |
| Determination of free inositols and other low molecular weight carbohydrates in vegetables. | Journal of agricultural and food chemistry 20110323 |
| Evidence of benzilic rearrangement during the electrochemical oxidation of D-glucose to D-glucaric acid. | Carbohydrate research 20110301 |
| Metabolic engineering of Escherichia coli for biotechnological production of high-value organic acids and alcohols. | Applied microbiology and biotechnology 20110201 |
| Evaluation of 99mTc-glucarate as a breast cancer imaging agent in a xenograft animal model. | Nuclear medicine and biology 20110201 |
| The role of MafA in regulating cytokine expression in pancreatic beta cells. | The Journal of biological chemistry 20110121 |
| Calcineurin/nuclear factor of activated T cells and MAPK signaling induce TNF-{alpha} gene expression in pancreatic islet endocrine cells. | The Journal of biological chemistry 20110114 |
| Evidence for reductive genome evolution and lateral acquisition of virulence functions in two Corynebacterium pseudotuberculosis strains. | PloS one 20110101 |
| Investigation of the Staphylococcus aureus GraSR regulon reveals novel links to virulence, stress response and cell wall signal transduction pathways. | PloS one 20110101 |
| Silver nanoparticles embedded in zeolite membranes: release of silver ions and mechanism of antibacterial action. | International journal of nanomedicine 20110101 |
| Efficacy of IV iron compared to oral iron for increment of haemoglobin level in anemic chronic kidney disease patients on erythropoietin therapy. | JNMA; journal of the Nepal Medical Association 20110101 |
| 99mTc-glucarate kinetics differentiate normal, stunned, hibernating, and nonviable myocardium in a perfused rat heart model. | European journal of nuclear medicine and molecular imaging 20101001 |
| Bis(imidazolium) galacta-rate dihydrate. | Acta crystallographica. Section E, Structure reports online 20100901 |
| The plastid hexokinase pHXK: a node of convergence for sugar and plastid signals in Arabidopsis. | FEBS letters 20100820 |
| Small-animal SPECT and SPECT/CT: application in cardiovascular research. | European journal of nuclear medicine and molecular imaging 20100801 |
| Use of modular, synthetic scaffolds for improved production of glucaric acid in engineered E. coli. | Metabolic engineering 20100501 |
| Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes. | Molecular bioSystems 20100501 |
| Micellar nanocarriers assembled from doxorubicin-conjugated amphiphilic macromolecules (DOX-AM). | Macromolecular bioscience 20100408 |
| Identification in Agrobacterium tumefaciens of the D-galacturonic acid dehydrogenase gene. | Applied microbiology and biotechnology 20100401 |
| Early hepatic insulin resistance in mice: a metabolomics analysis. | Molecular endocrinology (Baltimore, Md.) 20100301 |
| Calcium glucarate inhibits DMBA-induced oral carcinogenesis in the hamster: histomorphometric evaluation. | Anticancer research 20100301 |
| Synergistic effects of combined phytochemicals and skin cancer prevention in SENCAR mice. | Cancer prevention research (Philadelphia, Pa.) 20100201 |
| Toward engineering synthetic microbial metabolism. | Journal of biomedicine & biotechnology 20100101 |
| Complete genome sequence and comparative metabolic profiling of the prototypical enteroaggregative Escherichia coli strain 042. | PloS one 20100101 |
| Molecular mechanisms of hepatic fibrosis in non-alcoholic steatohepatitis. | Digestive diseases (Basel, Switzerland) 20100101 |
| Bioconversion of D-galacturonate to keto-deoxy-L-galactonate (3-deoxy-L-threo-hex-2-ulosonate) using filamentous fungi. | BMC biotechnology 20100101 |
| Genomic encyclopedia of sugar utilization pathways in the Shewanella genus. | BMC genomics 20100101 |
| A comparative study of antioxidative activity of calcium-D-glucarate, sodium-D-gluconate and D-glucono-1,4-lactone in a human blood platelet model. | Platelets 20100101 |
| Biology by design: from top to bottom and back. | Journal of biomedicine & biotechnology 20100101 |
| A genomic perspective on the potential of Actinobacillus succinogenes for industrial succinate production. | BMC genomics 20100101 |
| Hot transcriptomics. | Archaea (Vancouver, B.C.) 20100101 |
| De novo design of saccharide-peptide hydrogels as synthetic scaffolds for tailored cell responses. | Journal of the American Chemical Society 20091209 |
| Computation-facilitated assignment of the function in the enolase superfamily: a regiochemically distinct galactarate dehydratase from Oceanobacillus iheyensis . | Biochemistry 20091208 |
| Evaluation of patients with head and neck cancer by means of 99mTc-glucarate. | Journal of nuclear medicine technology 20091201 |
| Convenient large-scale synthesis of D-glucaro-1,4:6,3-dilactone. | The Journal of organic chemistry 20091106 |
| Significance of urinary glucaric acid measurement and its application to paclitaxel therapy. | Gan to kagaku ryoho. Cancer & chemotherapy 20091101 |
| Involvement of Per-Arnt-Sim Kinase and extracellular-regulated kinases-1/2 in palmitate inhibition of insulin gene expression in pancreatic beta-cells. | Diabetes 20090901 |
| A major role for perifornical orexin neurons in the control of glucose metabolism in rats. | Diabetes 20090901 |
| Resistin induces insulin resistance by both AMPK-dependent and AMPK-independent mechanisms in HepG2 cells. | Endocrine 20090801 |
| Synthetic protein scaffolds provide modular control over metabolic flux. | Nature biotechnology 20090801 |
| Synthetic metabolic pipelines. | Nature biotechnology 20090801 |
| Molecular imaging of cell death. | Methods (San Diego, Calif.) 20090601 |
| Functional states of the genome-scale Escherichia coli transcriptional regulatory system. | PLoS computational biology 20090601 |
| Comparison of cerebrospinal fluid obtained by ventricular endoscopy and by lumbar puncture in patients with hydrocephalus secondary to neurocysticercosis. | Surgical neurology 20090301 |
| In vitro evaluation of the chemoprotective action mechanisms of leontopodic acid against aflatoxin B1 and deoxynivalenol-induced cell damage. | Journal of applied toxicology : JAT 20090101 |
| Caffeic acid derivatives from Eupatorium perfoliatum L. | Molecules (Basel, Switzerland) 20081223 |
| The effect of high glucose on SERT, the human plasmalemmal serotonin transporter. | Nutritional neuroscience 20081201 |
| [The biological role of D-glucaric acid and its derivatives: potential use in medicine]. | Postepy higieny i medycyny doswiadczalnej (Online) 20080905 |
| Effect of the beta-glucuronidase inhibitor saccharolactone on glucuronidation by human tissue microsomes and recombinant UDP-glucuronosyltransferases. | The Journal of pharmacy and pharmacology 20080901 |
| Clinical applications of urinary organic acids. Part I: Detoxification markers. | Alternative medicine review : a journal of clinical therapeutic 20080901 |
| Effects of Mirasol PRT treatment on storage lesion development in plasma-stored apheresis-derived platelets compared to untreated and irradiated units. | Transfusion 20080801 |
| Protective effects of D-glucaro-1,4-lactone against oxidative modifications in blood platelets. | Nutrition, metabolism, and cardiovascular diseases : NMCD 20080701 |
| Could 99mTc-glucarate be used to evaluate tumour necrosis? In vitro and in vivo studies in leukaemic tumour cell line U937. | European journal of nuclear medicine and molecular imaging 20080701 |
| D-glucaro 1,4-lactone and resveratrol as antioxidants in blood platelets. | Cell biology and toxicology 20080401 |
| Quorum sensing detected by atomic force microscopy imaging of corrals surrounding multicellular arrangement of bacteria. | Microscopy research and technique 20080201 |
| Evaluating the protective role of ischaemic preconditioning in rat hearts using a stationary small-animal SPECT imager and 99mTc-glucarate. | Nuclear medicine communications 20080201 |
| [Improvement of urinary d-glucaric acid assay and its application]. | Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20080101 |
| Genomics of an extreme psychrophile, Psychromonas ingrahamii. | BMC genomics 20080101 |
| The genome of the versatile nitrogen fixer Azorhizobium caulinodans ORS571. | BMC genomics 20080101 |
| Relating gene expression data on two-component systems to functional annotations in Escherichia coli. | BMC bioinformatics 20080101 |
| Seasonal variation of trehalose and glycerol concentrations in winter snow-active insects. | Cryo letters 20080101 |
| Evolution of enzymatic activities in the enolase superfamily: L-talarate/galactarate dehydratase from Salmonella typhimurium LT2. | Biochemistry 20070821 |
| alpha-ketoglutaric semialdehyde dehydrogenase isozymes involved in metabolic pathways of D-glucarate, D-galactarate, and hydroxy-L-proline. Molecular and metabolic convergent evolution. | The Journal of biological chemistry 20070302 |
| (E)-metanicotine hemigalactarate (TC-2403-12) inhibits IL-8 production in cells of the inflamed mucosa. | International journal of colorectal disease 20070301 |
| Protective effects of D-glucaro 1,4-lactone against oxidative/nitrative modifications of plasma proteins. | Nutrition (Burbank, Los Angeles County, Calif.) 20070201 |
| GntR family of regulators in Mycobacterium smegmatis: a sequence and structure based characterization. | BMC genomics 20070101 |
| Induction of apoptosis by calcium D-glucarate in 7,12-dimethyl benz [a] anthracene-exposed mouse skin. | Journal of environmental pathology, toxicology and oncology : official organ of the International Society for Environmental Toxicology and Cancer 20070101 |
| Glycerate kinase of the hyperthermophilic archaeon Thermoproteus tenax: new insights into the phylogenetic distribution and physiological role of members of the three different glycerate kinase classes. | BMC genomics 20070101 |
| Esterification of select polyols with D-glucaric acid as model reactions for esterification of starch. | Carbohydrate research 20061127 |
| Ubiquitous presence of beta-glucuronidase (GUS) in plants and its regulation in some model plants. | Planta 20060901 |
| Tetranuclear copper(II) complexes bridged by alpha-D-glucose-1-phosphate and incorporation of sugar acids through the Cu4 core structural changes. | Inorganic chemistry 20060821 |
| (99m)Tc-glucarate imaging for the early detection of infarct in partially reperfused canine myocardium. | European journal of nuclear medicine and molecular imaging 20060301 |
| Nanoscale anionic macromolecules can inhibit cellular uptake of differentially oxidized LDL. | Biomacromolecules 20060201 |
| Detection of uronic oxidase activity in ripening peaches. | Phytochemistry 20060101 |
| Poly(glycoamidoamine)s for gene delivery: stability of polyplexes and efficacy with cardiomyoblast cells. | Bioconjugate chemistry 20060101 |
| Effect of antiepileptic drugs on the urinary excretion of porphyrins in non-porphyric subjects. | Journal of pharmacological sciences 20051201 |
| para-Hydrogenation of unsaturated moieties on poly(lysine) derived substrates for the development of novel hyperpolarized MRI contrast agents. | Organic & biomolecular chemistry 20051107 |
| Sleep loss: a novel risk factor for insulin resistance and Type 2 diabetes. | Journal of applied physiology (Bethesda, Md. : 1985) 20051101 |
| Biomarker measurements in a coastal fish-eating population environmentally exposed to organochlorines. | Environmental health perspectives 20051001 |
| Crystal structure and aqueous solubility of ammonium D-glucarate. | Carbohydrate research 20050926 |
| MRP-1 protein expression and glutathione content of in vitro tumor cell lines derived from human glioma carcinoma U-87-MG do not interact with 99mTc-glucarate uptake. | Cancer biotherapy & radiopharmaceuticals 20050801 |
| Generation of organic acids and monosaccharides by hydrolytic and oxidative transformation of food processing residues. | Bioresource technology 20050501 |
| Hydroxyl stereochemistry and amine number within poly(glycoamidoamine)s affect intracellular DNA delivery. | Journal of the American Chemical Society 20050309 |
| Possible induction of cholinesterase in epileptic patients treated with anticonvulsant drugs: relationship with lipoprotein levels. | Journal of clinical pharmacology 20040901 |
| 99mTc glucarate high-resolution imaging of drug sensitive and drug resistant human breast cancer xenografts in SCID mice. | Nuclear medicine communications 20040701 |
| High-resolution imaging with (99m)Tc-glucarate for assessing myocardial injury in rat heart models exposed to different durations of ischemia with reperfusion. | Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20040701 |
| New poly(d-glucaramidoamine)s induce DNA nanoparticle formation and efficient gene delivery into mammalian cells. | Journal of the American Chemical Society 20040623 |
| Vanadium(IV,V) complexes of D-saccharic and mucic acids in aqueous solution. | Dalton transactions (Cambridge, England : 2003) 20040621 |
| Iron(III) complexing ability of carbohydrate derivatives. | Journal of inorganic biochemistry 20040601 |
| Modulation of carcinogen metabolism and DNA interaction by calcium glucarate in mouse skin. | Toxicological sciences : an official journal of the Society of Toxicology 20040501 |
| Mechanisms of lung cancer chemoprevention by D-glucarate. | Chest 20040501 |
| Modulation of biomarkers during chemoprevention of mouse lung tumorigenesis by D-glucarate. | Chest 20040501 |
| Early detection of infarct in reperfused canine myocardium using 99mTc-glucarate. | Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20040401 |
| AlIII ion complexes of saccharic acid and mucic acid: a solution and solid-state study. | Chemistry (Weinheim an der Bergstrasse, Germany) 20040305 |
| Phosphotransferase-mediated transport of the osmolyte 2-O-alpha-mannosyl-D-glycerate in Escherichia coli occurs by the product of the mngA (hrsA) gene and is regulated by the mngR (farR) gene product acting as repressor. | The Journal of biological chemistry 20040213 |
| Decolorization of synthetic dyes using a copper complex with glucaric acid. | Chemosphere 20040101 |
| First synthesis of double headed 1,3,4-oxadiazino[6,5-b]indole acyclo C-nucleosides. | Nucleosides, nucleotides & nucleic acids 20040101 |
| Assessment of copper status in epileptic patients treated with anticonvulsant drugs by measuring the specific oxidase activity of ceruloplasmin. | Epilepsy research 20031001 |
| Relationship between PCBs in blood and D-glucaric acid in urine. | Toxicology letters 20030915 |
| Detoxifying cancer causing agents to prevent cancer. | Integrative cancer therapies 20030601 |
| Accumulation of technetium-99m glucarate: in vitro cell cultures and in vivo tumour models. | Nuclear medicine communications 20030501 |
| Non-invasive in vivo imaging of myocardial apoptosis and necrosis. | European journal of nuclear medicine and molecular imaging 20030401 |
| The first fluorescent sensor for D-glucarate based on the cooperative action of boronic acid and guanidinium groups. | Chemical communications (Cambridge, England) 20030321 |
| Calcium glucarate prevents tumor formation in mouse skin. | Biomedical and environmental sciences : BES 20030301 |
| Myocardial kinetics of Tc-99m glucarate in low flow, hypoxia, and aglycemia. | Journal of nuclear cardiology : official publication of the American Society of Nuclear Cardiology 20030101 |
| [Experimental systemic enzyme therapy of gouty and primary glomerulonephritis]. | Eksperimental'naia i klinicheskaia farmakologiia 20030101 |
| Differential effects of Saint John's Wort (hypericum perforatum) on the urinary excretion of D-glucaric acid and 6beta-hydroxycortisol in healthy volunteers. | European journal of clinical pharmacology 20021201 |
| Co-ordination of transition metal ions by galactaric acid: a potentiometric and spectroscopic study. | Journal of inorganic biochemistry 20021111 |
| [A study of some indirect biochemical markers in the evaluation of enzymatic induction caused by antiepileptic drugs]. | Revista de neurologia 20021001 |
| Calcium-D-glucarate. | Alternative medicine review : a journal of clinical therapeutic 20020801 |
| Determination of the side-products formed during the nitroxide-mediated bleach oxidation of glucose to glucaric acid. | Carbohydrate research 20020605 |
| Identification and characterization of the Bacillus subtilis D-glucarate/galactarate utilization operon ycbCDEFGHJ. | FEMS microbiology letters 20020507 |
| D-glucaric acid in common duct bile and relation to choledocholithiasis. | Scandinavian journal of gastroenterology 20020401 |
| 99mTc-glucarate for detection of isoproterenol-induced myocardial infarction in rats. | International journal of pharmaceutics 20020221 |
| Relationship between changes in drug score, D-glucaric acid excretion, and gamma-glutamyltransferase and beta-glucuronidase serum activities during anticonvulsant treatment. | Clinical laboratory 20020101 |
| Indium 111 antimyosin and Tc-99m glucaric acid for noninvasive identification of oncotic and apoptotic myocardial necrosis. | Journal of nuclear cardiology : official publication of the American Society of Nuclear Cardiology 20020101 |
| Sugar complexes with metal(2+) ions: thermodynamic parameters of associations of Ca(2+), Mg(2+) and Zn(2+) with galactaric acid. | Carbohydrate research 20011101 |
| Facile nitroxide-mediated oxidations of D-glucose to D-glucaric acid. | Carbohydrate research 20011101 |
| New possibilities in scintigraphy detection of carbon monoxide cardiotoxicity. | Przeglad lekarski 20010101 |
Related Products
Featured Products
© 2019 Angene International Limited. All rights Reserved.