Home Other Building Blocks {[(3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid

{[(3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid

CAS No.:
488-69-7
Catalog Number:
AG00393R
Molecular Formula:
C6H14O12P2
Molecular Weight:
340.1157
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
10g
95%
In Stock USA
United States
$200
- +
50g
95%
In Stock USA
United States
$600
- +
Product Description
Catalog Number:
AG00393R
Chemical Name:
{[(3S,4S,5R)-2,3,4-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid
CAS Number:
488-69-7
Molecular Formula:
C6H14O12P2
Molecular Weight:
340.1157
MDL Number:
MFCD06794967
IUPAC Name:
[(2R,3S,4S)-3,4,5-trihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]methyl dihydrogen phosphate
InChI:
InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6?/m1/s1
InChI Key:
RNBGYGVWRKECFJ-VRPWFDPXSA-N
SMILES:
O[C@@H]1[C@@H](COP(=O)(O)O)OC([C@H]1O)(O)COP(=O)(O)O
EC Number:
207-683-6
Properties
Complexity:
428  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0
Exact Mass:
339.996g/mol
Formal Charge:
0
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
7  
Isotope Atom Count:
0
Molecular Weight:
340.114g/mol
Monoisotopic Mass:
339.996g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
203A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
-5.6  
Literature
Title Journal
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Characterization of the high-affinity uptake of fructose-1,6-bisphosphate by cardiac myocytes. Molecular and cellular biochemistry 20120701
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Ultrasensitive regulation of anapleurosis via allosteric activation of PEP carboxylase. Nature chemical biology 20120601
Neurotrophic effects of magnesium fructose 1, 6-diphosphate on cortical neurons. The International journal of neuroscience 20120501
Strontium fructose 1,6-diphosphate prevents bone loss in a rat model of postmenopausal osteoporosis via the OPG/RANKL/RANK pathway. Acta pharmacologica Sinica 20120401
Fructose-1,6-bisphosphate attenuates induction of nitric oxide synthase in microglia stimulated with lipopolysaccharide. Life sciences 20120227
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Differential function of protective agents at each stage of the hypothermic preservation of hepatocytes. Journal of biochemistry 20110601
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Crystallization and preliminary X-ray characterization of the glpX-encoded class II fructose-1,6-bisphosphatase from Mycobacterium tuberculosis. Acta crystallographica. Section F, Structural biology and crystallization communications 20110601
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Metabolomics of supragingival plaque and oral bacteria. Journal of dental research 20101201
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Structure and activity of the metal-independent fructose-1,6-bisphosphatase YK23 from Saccharomyces cerevisiae. The Journal of biological chemistry 20100702
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Beneficial effects of fructose 1,6-biphosphate on hypothermia-induced reactive oxygen species injury in rats. European journal of pharmacology 20080820
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Effect of fructose-1,6-bisphosphate in the cold storage solution after 12 and 36 hours of rat liver preservation. Transplantation proceedings 20041101
Cloning and expression of the Clostridium thermocellum L-lactate dehydrogenase gene in Escherichia coli and enzyme characterization. Canadian journal of microbiology 20041001
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Physiological effects of intravenous fructose 1.6-diphosphate on diaphragmatic function in malnourished patients with COPD. Monaldi archives for chest disease = Archivio Monaldi per le malattie del torace 20040101
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Proton transport in maize tonoplasts supported by fructose-1,6-bisphosphate cleavage. Pyrophosphate-dependent phosphofructokinase as a pyrophosphate-regenerating system. Plant physiology 20031001
Enzymes of glycolysis are functionally associated with the mitochondrion in Arabidopsis cells. The Plant cell 20030901
4-hydroxy-2,5-dimethyl-3(2H)-furanone formation by Zygosaccharomyces rouxii: effect of the medium. Journal of agricultural and food chemistry 20030730
The HPr(Ser) kinase of Streptococcus salivarius: a hexameric bifunctional enzyme controlled by glycolytic intermediates and inorganic phosphate. FEMS microbiology letters 20030715
Effects of n-3 fatty acid, fructose-1,6-diphosphate and glutamine on mucosal cell proliferation and apoptosis of small bowel graft after transplantation in rats. World journal of gastroenterology 20030615
Regulation and mutational analysis of the HPr kinase/phosphorylase from Bacillus subtilis. Biochemistry 20030610
Intravenous toxicity of fructose-1,6-bisphosphate in rats. Toxicology letters 20030605
Fluorescence study of ligand binding to potato tuber pyrophosphate-dependent phosphofructokinase: evidence for competitive binding between fructose-1,6-bisphosphate and fructose-2,6-bisphosphate. Archives of biochemistry and biophysics 20030601
Purification and characterization of pyrophosphate- and ATP-dependent phosphofructokinases from banana fruit. Planta 20030501
Using fructose-1,6-diphosphate during hypothermic rabbit-heart preservation: a high-energy phosphate study. The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation 20030501
Effects of sodium magnesium fructose diphosphate on free calcium concentration and nitric oxide synthase activity of ischemic synaptosome. Yao xue xue bao = Acta pharmaceutica Sinica 20030501
Linkage between fructose 1,6-bisphosphate binding and the dimer-tetramer equilibrium of Escherichia coli glycerol kinase: critical behavior arising from change of ligand stoichiometry. Biochemistry 20030415
Characterization of myoglobin toxicity in renal cortical slices from Fischer 344 rats. Toxicology 20030303
Regulation of the central glycolytic genes in Bacillus subtilis: binding of the repressor CggR to its single DNA target sequence is modulated by fructose-1,6-bisphosphate. Molecular microbiology 20030301
Fructose-1,6-bisphosphate for improved outcome after hypothermic circulatory arrest in pigs. The Journal of thoracic and cardiovascular surgery 20030301
Variations in the response of mouse isozymes of adenylosuccinate synthetase to inhibitors of physiological relevance. The Journal of biological chemistry 20030227
Fructose-1,6-biphosphate prevents excitotoxic neuronal cell death in the neonatal mouse brain. Brain research. Developmental brain research 20030216
Immunomodulatory effect of fructose-1,6-bisphosphate on T-lymphocytes. International immunopharmacology 20030201
Fructose-1,6-bisphosphate preserves intracellular glutathione and protects cortical neurons against oxidative stress. Brain research 20030117
Fructose-1,6-biphosphate and nucleoside pool modifications prevent neutrophil accumulation in the reperfused intestine. Journal of leukocyte biology 20030101
An assessment of fructose-1,6-bisphosphate as an antimicrobial and anti-inflammatory agent in sepsis. Pharmacological research 20030101
Effects of fructose-1,6-bisphosphate on morphological and functional neuronal integrity in rat hippocampal slices during energy deprivation. Neuroscience 20030101
Emetine inhibits glycolysis in isolated, perfused rat hearts. Cardiovascular toxicology 20030101
Fructose diphosphate attenuates the acetaminophen-induced liver injury in the rat evidence for involvement of nitric oxide. Research communications in molecular pathology and pharmacology 20030101
Activation of the neuroprotective ERK signaling pathway by fructose-1,6-bisphosphate during hypoxia involves intracellular Ca2+ and phospholipase C. Brain research 20021220
Fructose-1,6-diphosphate alone and in combination with cyclosporine potentiates rat cardiac allograft survival and inhibits lymphocyte proliferation and interleukin-2 expression. Transplantation 20021215
Glucose metabolites inhibit protein phosphatases and directly promote insulin exocytosis in pancreatic beta-cells. Endocrinology 20021201
[Effect of neuroprotectant agent combined with cocktail on expression of anti-apoptotic protein bcl-2 in rats after focal cerebral ischemia]. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine] 20021101
Fructose-1,6-diphosphate attenuates prostaglandin E2 production and cyclo-oxygenase-2 expression in UVB-irradiated HaCaT keratinocytes. British journal of pharmacology 20021001
Fructose-1,6-Bisphosphate inhibits excess activation of Kupffer cell function induced by endotoxin. Digestive diseases and sciences 20021001
Storage solution containing fructose-1,6-bisphosphate inhibits the excess activation of Kupffer cells in cold liver preservation. Transplantation 20020927
Clotrimazole decreases glycolysis and the viability of lung carcinoma and colon adenocarcinoma cells. European journal of pharmacology 20020920
Physiopathological studies in septic rats and the use of fructose 1,6-bisphosphate as cellular protection. Critical care medicine 20020901
Destabilizing effects of fructose-1,6-bisphosphate on membrane bilayers. Lipids 20020901
Leishmania donovani phosphofructokinase. Gene characterization, biochemical properties and structure-modeling studies. European journal of biochemistry 20020801
[Research progress on the glycerol kinase]. Wei sheng wu xue bao = Acta microbiologica Sinica 20020801
Chemical formation of 4-hydroxy-2,5-dimethyl-3[2H]-furanone from D-fructose 1,6-diphosphate. Carbohydrate research 20020716
Fructose-1,6-diphosphate attenuates acute lung injury induced by ischemia-reperfusion in rats. Critical care medicine 20020701
Prevention of alpha-naphthylthiourea-induced pulmonary edema with fructose-1,6-diphosphate. Experimental lung research 20020601
Quantification of the influence of HPrSer46P on CcpA-cre interaction. Journal of molecular biology 20020524
Evaluation of fructose diphosphate in RBC preservation. Transfusion 20020301
[The protective mechanism of fructose-1, 6-diphosphate on ischemic brain injury]. Zhonghua yi xue za zhi 20020225
Molecular characterization of a phosphoenolpyruvate carboxylase from a thermophilic cyanobacterium, Synechococcus vulcanus with unusual allosteric properties. Plant & cell physiology 20020201
Kinetic and allosteric consequences of mutations in the subunit and domain interfaces and the allosteric site of yeast pyruvate kinase. Archives of biochemistry and biophysics 20020101
Ischemic stroke in elderly patients treated with a free radical scavenger-glycolytic intermediate solution: a preliminary pilot trial. Neurological research 20020101
An absolute requirement of fructose 1,6-bisphosphate for the Lactobacillus casei L-lactate dehydrogenase activity induced by a single amino acid substitution. Protein engineering 20020101
ADP-glucose pyrophosphorylase from wheat endosperm. Purification and characterization of an enzyme with novel regulatory properties. Planta 20020101
Time dependent responses of glycolytic intermediates in a detailed glycolytic model of Lactococcus lactis during glucose run-out experiments. Molecular biology reports 20020101
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Clinical and pharmaceutical management of deficiencies, excesses and infection with nutrition support. Current opinion in clinical nutrition and metabolic care 20010501
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Purification and characterization of pyruvate kinase from lamprey (Entosphenus japonicus) muscle. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20010101
Fructose, 1,6-diphosphate mitigates CCl4 suppressed nitric oxide synthase activity in rats. Indian journal of experimental biology 20010101
Caveolae and the organization of carbohydrate metabolism in vascular smooth muscle. Journal of cellular biochemistry 20010101
Protection from amphotericin B-induced lipid peroxidation in rats by fructose-1,6-diphosphate. Research communications in molecular pathology and pharmacology 19970201
Enzymatic assays of fructose-1-phosphate and fructose-1,6-bisphosphate in the picomole range. Analytical biochemistry 19960315
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