Chemistry:Fructose 6-phosphate

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Fructose 6-phosphate
Beta-D-fructose-6-phosphate wpmp.png
Fructose 6-phosphate.png
Names
IUPAC name
6-O-Phosphono-α-D-fructofuranose
Other names
β-D-fructose 6-phosphate,
fructose 6-phosphate
Identifiers
3D model (JSmol)
Abbreviations F6P
ChEBI
ChemSpider
KEGG
UNII
Properties
C6H13O9P
Molar mass 260.14 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Fructose 6-phosphate (sometimes called the Neuberg ester) is a derivative of fructose, which has been phosphorylated at the 6-hydroxy group. It is one of several possible fructosephosphates. The β-D-form of this compound is very common in cells.[1][2] The great majority of glucose is converted to fructose 6-phosphate upon entering a cell. Fructose is predominantly converted to fructose 1-phosphate by fructokinase following cellular import.

History

The name Neuberg ester comes from the German biochemist Carl Neuberg. In 1918, he found that the compound (later identified as fructose 6-phosphate) was produced by mild acid hydrolysis of fructose 2,6-bisphosphate.[3]

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 α-D-fructose 6-phosphate Phosphofructokinase-1 α-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
75px 75px
Pi H2O
   
  Phosphoglucose isomerase   Fructose bisphosphatase

Compound C00668 at KEGG Pathway Database. Enzyme 5.3.1.9 at KEGG Pathway Database. Compound C05345 at KEGG Pathway Database. Enzyme 2.7.1.11 at KEGG Pathway Database. Enzyme 3.1.3.11 at KEGG Pathway Database. Reaction [1] at KEGG Pathway Database. Compound C05378 at KEGG Pathway Database.


See also


References

  1. Berg, Jeremy M.; Tymoczko, Stryer (2002). Biochemistry (5th ed.). New York: W.H. Freeman and Company. ISBN 0-7167-3051-0. https://archive.org/details/biochemistrychap00jere. 
  2. Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN:1-57259-153-6.
  3. Fruton, Joseph S. Proteins, Enzymes, Genes: The Interplay of Chemistry and Biology. Yale University Press: New Haven, 1999. p 292