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Fructose 6-phosphate

From Wikipedia, the free encyclopedia
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)
AbbreviationsF6P
ChEBI
ChemSpider
ECHA InfoCard100.010.360Edit this at Wikidata
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 mass260.14 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Fructose 6-phosphate (sometimes called theNeuberg ester) is a derivative offructose, which has beenphosphorylated at the 6-hydroxy group. It is one of several possiblefructosephosphates. The β-D-form of this compound is very common incells.[1][2] The great majority ofglucose is converted to fructose 6-phosphate upon entering a cell.Fructose is predominantly converted tofructose 1-phosphate byfructokinase following cellular import.

History

[edit]

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

In glycolysis

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Fructose 6-phosphate lies within theglycolysismetabolic pathway and is produced by isomerisation ofglucose 6-phosphate. It is in turn further phosphorylated tofructose-1,6-bisphosphate.

α-D-glucose 6-phosphatePhosphoglucose isomeraseβ-D-fructose 6-phosphatePhosphofructokinase-1β-D-fructose 1,6-bisphosphate
  
ATPADP
PiH2O
  
 Phosphoglucose isomerase Fructose bisphosphatase

CompoundC00668 atKEGG Pathway Database.Enzyme5.3.1.9 atKEGG Pathway Database.CompoundC05345 atKEGG Pathway Database.Enzyme2.7.1.11 atKEGG Pathway Database.Enzyme3.1.3.11 atKEGG Pathway Database.Reaction[1] atKEGG Pathway Database.CompoundC05378 atKEGG Pathway Database.

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

  1. ^The interactive pathway map can be edited at WikiPathways:"GlycolysisGluconeogenesis_WP534".


See also

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References

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  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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