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Merck

F6803

Sigma-Aldrich

D-Fruktose 1,6-Bisphosphat Trinatriumsalz

≥98% (TLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C6H11Na3O12P2 · xH2O
CAS-Nummer:
Molekulargewicht:
406.06 (anhydrous basis)
MDL-Nummer:
UNSPSC-Code:
12352201
PubChem Substanz-ID:
NACRES:
NA.25

Biologische Quelle

microbial

Qualitätsniveau

Assay

≥98% (TLC)

Form

powder

Methode(n)

thin layer chromatography (TLC): suitable

Farbe

white to off-white

Löslichkeit

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

Kationenspuren

Na: 14.6-18.8% (dry basis)

Lagertemp.

−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

InChIKey

ISLNIFDAODOXHN-GNWSQLALSA-K

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Anwendung

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. Wirkung

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.

Sonstige Hinweise

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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
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
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

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