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Fructose 6-phosphate

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
   
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 [1] at KEGG Pathway Database. Compound C05378 at KEGG Pathway Database.

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

  • Phosphofructokinase 2 is Fructose 2,6-bisphosphate. This is one of the regulatory reactions of glycolysis.
  • Mannose phosphate isomerase creates mannose-6-phosphate.
 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

  1. ^ Fruton, Joseph S. Proteins, Enzymes, Genes: The Interplay of Chemistry and Biology. Yale University Press: New Haven, 1999. p 292
This metabolism related chemical article is a stub. You can help Wikipedia by expanding it.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Fructose_6-phosphate". A list of authors is available in Wikipedia.

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