Fructose 6-phosphate

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Fructose 6-phosphate
IUPAC name [(2R,3R,4S)-3,4,5-trihydroxy-5-
(hydroxymethyl)oxolan-2-yl]
methoxyphosphonic acid
Other names β-D-fructose 6-phosphate,
fructose 6-phosphate
Abbreviations F6P
Molecular formula C6H13O9P
Molar mass 262.1535 g/mol
CAS number 643-13-0
SMILES O1C(CO)(O)C(O)C(O)C1COP
(O)(O)=O
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Fructose 6-phosphate (also known as the Neuberg ester) is fructose sugar phosphorylated on carbon 6 (ie. is a fructosephosphate). The β-D-form of this compound is very common in cells, the vast majority of glucose and fructose entering a cell will become converted to this at some point. The name Neuberg ester comes from the German biochemist Carl Neuberg.

Contents

History

In 1918, Carl Neuberg found that the compound (only later identified as fructose 6-phosphate) could be produced by mild acid hydrolysis of "Harden-Young ester" (fructose 2,6-bisphosphate).[1]

Fructose 6-phosphate in glycolysis

Fructose 6-phosphate lies within the glycolysis metabolic pathway and is produced by isomerisation of glucose 6-phosphate. It is in turn further phosphorylated to fructose-1,6-bisphosphate.

α-D-glucose 6-phosphate Phosphoglucose isomerase β-D-fructose 6-phosphate Phosphofructokinase-1 β-D-fructose 1,6-bisphosphate
image:alpha-D-glucose-6-phosphate_wpmp.png   image:beta-D-fructose-6-phosphate_wpmp.png   image:beta-D-fructose-1,6-bisphosphate_wpmp.png
ATP ADP
Pi H2O
   
  Phosphoglucose isomerase   Fructose bisphosphatase


Fructose 6-phosphate isomerism

Main article: Fructose

Fructose 6-phosphate has only one biologically active isomer, the β-D-form. There are many other isomers, analogous to those of fructose.

See also

 v  d  e 
Glycolysis Metabolic Pathway
Glucose Hexokinase Glucose-6-phosphate Phosphoglucoisomerase Fructose 6-phosphate Phosphofructokinase Fructose 1,6-bisphosphate Fructose bisphosphate aldolase Dihydroxyacetone phosphate Glyceraldehyde 3-phosphate Triosephosphate isomerase Glyceraldehyde 3-phosphate Glyceraldehyde phosphate dehydrogenase
ATP ADP ATP ADP NAD+ + Pi NADH + H+
+ 2
NAD+ + Pi NADH + H+
1,3-Bisphosphoglycerate Phosphoglycerate kinase 3-Phosphoglycerate Phosphoglycerate mutase 2-Phosphoglycerate Enolase Phosphoenolpyruvate Pyruvate kinase Pyruvate Pyruvate dehydrogenase Acetyl-CoA
ADP ATP H2O ADP ATP CoA + NAD+ NADH + H+ + CO2
2 2 2 2 2 2
ADP ATP H2O

References

Template:Metabolic pathway stub

de:Fructose-6-Phosphat


Acknowledgement and Attribution Regarding Sources of Content

Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .

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