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F6803 Sigma-Aldrich

D-Fructose 1,6-bisphosphate trisodium salt hydrate

≥98% (TLC)

Synonym: D(+)Fructofuranose 1,6-diphosphate trisodium salt hydrate, Harden-Young ester, Hexose diphosphate trisodium salt hydrate

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Properties

Related Categories Aerobic Glycolysis (the Warburg Effect), Biochemicals and Reagents, Cancer Metabolism, Cancer Research, Carbohydrates,
Quality Level   200
biological source   microbial
assay   ≥98% (TLC)
form   powder
application(s)   thin layer chromatography (TLC): suitable
storage temp.   −20°C
SMILES string   O.[Na+].[Na+].[Na+].O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H](O)C(=O)COP(O)([O-])=O
InChI   1S/C6H14O12P2.3Na.H2O/c7-3(1-17-19(11,12)13)5(9)6(10)4(8)2-18-20(14,15)16;;;;/h3,5-7,9-10H,1-2H2,(H2,11,12,13)(H2,14,15,16);;;;1H2/q;3*+1;/p-3/t3-,5-,6-;;;;/m1..../s1
InChI key   ISLNIFDAODOXHN-GNWSQLALSA-K

Description

Application

D-Fructose-1,6-bisphosphate (FBP), a common metabolic sugar, is the precursor of glyceraldehyde 3-phosphate and dihydroxyacetone phosphate in the glycolytic pathway. It may be used as an allosteric activator of enzymes such as pyruvate kinase and NAD+-dependent L-(+)-lactate dehydrogenase, as an inhibitor of acetate kinase and as a substrate to identify and characterize enzymes such as fructose-1,6-bisphosphate aldolase(s) and fructose-1,6-bisphosphatase(s). FBP is studied as a neuroprotective agent in brain injury.

Packaging

1, 5 g in poly bottle

10 mg in glass bottle

Biochem/physiol Actions

Fructose-1,6-biphosphate (F1,6P) is a glycolytic intermediate produced by the transfer of a phosphate from ATP to fructose-6-phosphate by the enzyme phosphofructokinase. Fructose-1,6-biphosphate, along with fructose-2,6-biphosphate, modulates the activity of phosphofructokinase-1 (PFK-1), the rate-limiting step in glycolysis. During glycolysis, aldolase splits Fructose-1,6-biphosphate into dihydroxacetone phosphate (DHAP) and glyceraldehyde phosphate. Fructose-1,6-biphosphate is also an allosteric activator of the M2 isoform of Pyruvate Kinase (PK-M2), the predominant form of pyruvate kinase in cancer cells.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Aerobic Glycolysis and the Warburg Effect

The Warburg effect is the enhanced conversion of glucose to lactate observed in tumor cells, even in the presence of normal levels of oxygen. Otto Heinrich Warburg demonstrated in 1924 that cancer ce...
BioFiles v7 n4
Keywords: Aerobic, Cancer, Cell proliferation, Clinical, Glycolysis, Phosphorylations, Transcription

Glycolysis via the Embden-Meyerhof-Parnas glycolytic pathway

Glycolysis is the almost universal pathway that converts glucose into pyruvate along with the formation of nicotinamide adenine dinucleotide (NADH) and adenosine triphosphate (ATP). It primarily occu...
Keywords: Aerobic, Aldol reaction, Anaerobic, Dehydration reaction, Fermentation, Glycolysis, Isomerizations, Metabolism, Metabolites, Metabolomics, Oxidations, Phosphorylations, Photosynthesis

Peer-Reviewed Papers
15

References

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