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F0752

Sigma-Aldrich

D-Fructose 1,6-bisphosphate tetra(cyclohexylammonium) salt

≥95% anhydrous basis (enzymatic)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H14O12P2 · 4C6H13N
CAS Number:
103213-44-1
Molecular Weight:
736.81
UNSPSC Code:
12352201
PubChem Substance ID:
329799667
NACRES:
NA.25

biological source

synthetic (organic)

Quality Level

200

Assay

≥95% anhydrous basis (enzymatic)

form

powder

impurities

Hexose monophosphates, essentially free

color

white to off-white

solubility

water: 100 mg/mL, clear to hazy, colorless to faintly yellow

storage temp.

−20°C

SMILES string

NC1CCCCC1.NC2CCCCC2.NC3CCCCC3.NC4CCCCC4.O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)C(=O)COP(O)(O)=O

InChI

1S/4C6H13N.C6H14O12P2/c4*7-6-4-2-1-3-5-6;7-3(1-17-19(11,12)13)5(9)6(10)4(8)2-18-20(14,15)16/h4*6H,1-5,7H2;3,5-7,9-10H,1-2H2,(H2,11,12,13)(H2,14,15,16)/t;;;;3-,5-,6-/m....1/s1

InChI key

NVWGDAYGDKPKLQ-CBCSRFDDSA-N

Application

D-Fructose-1,6-bisphosphate (FBP) 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

D-Fructose-1,6-bisphosphate (FBP), a common metabolic sugar, is the precursor of glyceraldehyde 3-phosphate and dihydroxyacetone phosphate in the glycolytic pathway.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D-(−)-Fructose ≥99% (HPLC)

Sigma-Aldrich

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Sigma-Aldrich

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Scott D Pegan et al.
Journal of molecular biology, 386(4), 1038-1053 (2009-01-27)
Mycobacterium tuberculosis, the causative agent of tuberculosis (TB), currently infects one-third of the world's population in its latent form. The emergence of multidrug-resistant and extensive drug-resistant strains has highlighted the need for new pharmacological targets within M. tuberculosis. The class
Chao Wang et al.
Molecular biology reports, 39(4), 5017-5024 (2011-12-14)
This study investigated whether there were single nucleotide polymorphisms (SNPs) in fructose-1,6-bisphosphate aldolase (FBA) gene associated with growth traits of the clam Meretrix meretrix. A FBA gene was identified in M. meretrix and its deduced amino acid residues shared high
Javier Modrego et al.
Journal of vascular surgery, 55(4), 1124-1133 (2012-01-10)
The purpose of this study was to evaluate the expression of proteins related to cytoskeleton and energetic metabolism at abdominal aortic aneurysm (AAA) sites using proteomics. Several remodeling-related mechanisms have been associated with AAA formation but less is known about
Paul D van Poelje et al.
Handbook of experimental pharmacology, 203(203), 279-301 (2011-04-13)
Fructose-1,6-bisphosphatase (FBPase), a rate-controlling enzyme of gluconeogenesis, has emerged as an important target for the treatment of type 2 diabetes due to the well-recognized role of excessive endogenous glucose production (EGP) in the hyperglycemia characteristic of the disease. Inhibitors of
Paul D van Poelje et al.
Diabetes, 55(6), 1747-1754 (2006-05-30)
Gluconeogenesis is increased in type 2 diabetes and contributes significantly to fasting and postprandial hyperglycemia. We recently reported the discovery of the first potent and selective inhibitors of fructose 1,6-bisphosphatase (FBPase), a rate-controlling enzyme of gluconeogenesis. Herein we describe acute
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