Fructose 6-phosphate

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.

Fructose 6-phosphate
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
ECHA InfoCard 100.010.360
KEGG
UNII
  • InChI=1S/C6H13O9P/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)/t3-,4-,5+,6+/m1/s1 checkY
    Key: BGWGXPAPYGQALX-ZXXMMSQZSA-N checkY
  • InChI=1/C6H13O9P/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)/t3-,4-,5+,6+/m1/s1
    Key: BGWGXPAPYGQALX-ZXXMMSQZBI
  • O=P(O)(O)OC[C@H]1O[C@@](O)(CO)[C@@H](O)[C@@H]1O
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).
☒N verify (what is checkY☒N ?)
Infobox references

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
   
ATP ADP
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 at KEGG Pathway Database. Compound C05378 at KEGG Pathway Database.

Click on genes, proteins and metabolites below to link to respective articles.[§ 1]

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GlycolysisGluconeogenesis_WP534
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GlycolysisGluconeogenesis_WP534
|alt=Glycolysis and Gluconeogenesis edit]]
Glycolysis and Gluconeogenesis edit
  1. The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".


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.
  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
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