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F3627

Sigma-Aldrich

D-Fructose 6-phosphate disodium salt hydrate

≥98%, amorphous powder

Synonym(s):

Sodium (2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl phosphate

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About This Item

Empirical Formula (Hill Notation):
C6H11Na2O9P · xH2O
CAS Number:
26177-86-6
Molecular Weight:
304.10 (anhydrous basis)
Beilstein/REAXYS Number:
5686786
MDL number:
MFCD16661244
UNSPSC Code:
12352201
PubChem Substance ID:
329799699
NACRES:
NA.25

biological source

bacterial (Corynebacterium)

Quality Level

300

assay

≥98%

form

amorphous powder

impurities

<0.05 mol % fructose 1,6-diphosphate
<1.5 mol % glucose 6-phosphate

color

white to off-white

solubility

H2O: 100 mg/mL, clear to slightly hazy, colorless to faintly yellow

cation traces

Na: 14.6-15.6% (dry basis)

application(s)

agriculture

storage temp.

−20°C

SMILES string

O.[Na+].[Na+].OC[C@@]1(O)O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@@H]1O

InChI

1S/C6H13O9P.2Na.H2O/c7-2-6(10)5(9)4(8)3(15-6)1-14-16(11,12)13;;;/h3-5,7-10H,1-2H2,(H2,11,12,13);;;1H2/q;2*+1;/p-2/t3-,4-,5+,6-;;;/m1.../s1

InChI key

VSCMQICEHMPOEC-HTKRKRNRSA-L

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Application

D-Fructose 6-phosphate (F6P) is a sugar intermediate of the glycolytic pathway that may be used to help identify, differentiate and characterize enzymes such as phosphofructokinase(s), pyrophosphate-dependent fructose-6-phosphate 1-phosphotransferase(s), D-fructose-6-phosphate aldolase(s), glutamine:fructose-6-phosphate amidotransferase(s) and glucosamine-6P synthase(s).

Biochem/physiol Actions

Fructose-6-phosphate is a glycolytic intermediate produced by the isomerization of glucose-6-phosphate by phosphoglucoisomerase.

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Yimin Qian et al.
Bioorganic & medicinal chemistry letters, 21(21), 6264-6269 (2011-10-01)
Through high throughput screening and subsequent hit identification and optimization, we synthesized a series of 1-arylcarbonyl-6,7-dimethoxyisoquinoline derivatives as the first reported potent and reversible GFAT inhibitors. SAR studies of this class of compounds indicated significant impact on GFAT inhibition potency
Kay O Broschat et al.
The Journal of biological chemistry, 277(17), 14764-14770 (2002-02-14)
Glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines in mammals. A member of the N-terminal nucleophile class of amidotransferases, GFAT transfers the amino group from the L-glutamine amide to D-fructose 6-phosphate, producing glutamic
Wai Yee Phong et al.
PloS one, 8(2), e56037-e56037 (2013-02-15)
Metabolic versatility has been increasingly recognized as a major virulence mechanism that enables Mycobacterium tuberculosis to persist in many microenvironments encountered in its host. Glucose is one of the most abundant carbon sources that is exploited by many pathogenic bacteria
Philippe Durand et al.
Archives of biochemistry and biophysics, 474(2), 302-317 (2008-02-19)
L-Glutamine:d-fructose-6-phosphate amidotransferase, also known as glucosamine-6-phosphate synthase (GlcN6P synthase), which catalyzes the first step in a pathway leading to the formation of uridine 5'-diphospho-N-acetyl-d-glucosamine (UDP-GlcNAc), is a key point in the metabolic control of the biosynthesis of amino sugar-containing macromolecules.
S Y But et al.
Biochemistry. Biokhimiia, 77(4), 372-377 (2012-07-20)
In the cluster of genes for sucrose biosynthesis and cleavage in Methylomicrobium alcaliphilum 20Z, a gene whose encoded sequence showed high similarity to sugar kinases of the ribokinase family was found. By heterologous expression of this gene in Escherichia coli
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