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