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F6803

Sigma-Aldrich

D-Fructose 1,6-bisphosphate trisodium salt hydrate

≥98% (TLC)

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C6H11Na3O12P2 · xH2O
Numero CAS:
38099-82-0
Peso molecolare:
406.06 (anhydrous basis)
Numero MDL:
MFCD03427650
Codice UNSPSC:
12352201
ID PubChem:
24894921
NACRES:
NA.25

Origine biologica

microbial

Livello qualitativo

200

Saggio

≥98% (TLC)

Forma fisica

powder

tecniche

thin layer chromatography (TLC): suitable

Colore

white to off-white

Solubilità

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

Cationi in tracce

Na: 14.6-18.8% (dry basis)

Temperatura di conservazione

−20°C

Stringa SMILE

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
ISLNIFDAODOXHN-GNWSQLALSA-K

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Applicazioni

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.

Azioni biochim/fisiol

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.

Altre note

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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Sigma-Aldrich

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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
Yasmean Kalam et al.
Clinical toxicology (Philadelphia, Pa.), 50(7), 546-554 (2012-08-09)
Fructose-1,6-diphosphate (FDP) is a metabolite in the glycolytic pathway created from glucose. Exogenously administered FDP increases the yield of ATP from anaerobic glycolysis. FDP reduces ischaemic tissue area in experimentally-induced cerebral and myocardial infarction and improves haemodynamics post-cardiac bypass. We
Laura Novellasdemunt et al.
The Journal of biological chemistry, 288(15), 10640-10651 (2013-03-05)
Reciprocal regulation of metabolism and signaling allows cells to modulate their activity in accordance with their metabolic resources. Thus, amino acids could activate signal transduction pathways that control cell metabolism. To test this hypothesis, we analyzed the effect of amino
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