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
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.

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
Alpha-D-glucose-6-phosphate wpmp.png   Beta-D-fructose-6-phosphate wpmp.png   Beta-D-fructose-1,6-bisphosphate wpmp.png
ATP ADP
Biochem reaction arrow reversible NNNN horiz med.png Biochem reaction arrow reversible YYYY horiz med.png
Pi H2O
   
  Phosphoglucose isomerase   Fructose bisphosphatase


Fructose 6-phosphate isomerism

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


References

  1. Fruton, Joseph S. Proteins, Enzymes, Genes: The Interplay of Chemistry and Biology. Yale University Press: New Haven, 1999. p 292

Template:Metabolic pathway stub

de:Fructose-6-Phosphat


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