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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)

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)

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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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