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F6803

D-Fructose 1,6-bisphosphate trisodium salt hydrate

≥98% (TLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H11Na3O12P2 · xH2O
CAS Number:
38099-82-0
Molecular Weight:
406.06 (anhydrous basis)
NACRES:
NA.25
PubChem Substance ID:
24894921
UNSPSC Code:
12352201
MDL number:
MFCD03427650
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biological source

microbial

Quality Level

200

assay

≥98% (TLC)

form

powder

technique(s)

thin layer chromatography (TLC): suitable

color

white to off-white

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

cation traces

Na: 14.6-18.8% (dry basis)

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

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.

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. 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.
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.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000511411
0000511405
0000511411
0000511405
0000510333

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Articles

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Aerobic Glycolysis and the Warburg Effect

Warburg effect enhances glucose to lactate conversion in tumor cells, regardless of oxygen levels; impacting cancer metabolism since 1924.

Tao Yu et al.
Cell, 174(6), 1549-1558 (2018-08-14)
Engineering microorganisms for production of fuels and chemicals often requires major re-programming of metabolism to ensure high flux toward the product of interest. This is challenging, as millions of years of evolution have resulted in establishment of tight regulation of
Lei Lv et al.
Molecular cell, 52(3), 340-352 (2013-10-15)
Alternative splicing of the PKM2 gene produces two isoforms, M1 and M2, which are preferentially expressed in adult and embryonic tissues, respectively. The M2 isoform is reexpressed in human cancer and has nonmetabolic functions in the nucleus as a protein
Thomas J Wheeler et al.
Molecular and cellular biochemistry, 366(1-2), 31-39 (2012-03-20)
Previously, we reported that fructose-1,6-bisphosphate (FBP) was taken up by rat cardiac myocytes by two processes: a component that was saturable at micromolar levels and a nonsaturable component that dominated at millimolar levels. Here, we continued to characterize the saturable
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