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F6803

Sigma-Aldrich

D-Fructose 1,6-bisphosphate trisodium salt hydrate

≥98% (TLC)

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Synonym(s):
D(+)Fructofuranose 1,6-diphosphate trisodium salt hydrate, Harden-Young ester, Hexose diphosphate trisodium salt hydrate
Empirical Formula (Hill Notation):
C6H11Na3O12P2 · xH2O
CAS Number:
38099-82-0
Molecular Weight:
406.06 (anhydrous basis)
MDL number:
MFCD03427650
PubChem Substance ID:
24894921
NACRES:
NA.25

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

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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. 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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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Roberto Christ Vianna Santos et al.
Inflammation, 35(3), 1198-1203 (2012-02-14)
It has been previously showed that fructose-1,6-bisphosphate (FBP) has anti-inflammatory and immunomodulatory effects on several experimental inflammation models. However, the effects and mechanism of FBP on Zymosan-induced acute lung injury (ALI) in mice had not been tested. In this study
Guilherme Vargas Bochi et al.
Inflammation, 35(6), 1786-1792 (2012-07-11)
The accumulation of advanced oxidation protein products (AOPP) has been linked to several pathological conditions. Previous studies have identified AOPP as a novel biomarker of oxidative damage to proteins and a novel class of mediator of inflammation. The aim of
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
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
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
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