Fructose 6-phosphate
5712191
210656694
2008-05-06T21:04:49Z
Rockfang
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changing stub name per [[Wikipedia:Stub_types_for_deletion/Log/2008/March/19|SfD]] using [[Project:AutoWikiBrowser|AWB]]
{{chembox new
| ImageFile = beta-D-fructose-6-phosphate_wpmp.png
| ImageSize = 150px
| IUPACName = [(2R,3R,4S)-3,4,5-trihydroxy-5-<br>(hydroxymethyl)oxolan-2-yl]<br>methoxyphosphonic acid
| OtherNames = β-D-fructose 6-phosphate, <br>fructose 6-phosphate
| Abbreviations = F6P
| Formula = C<sub>6</sub>H<sub>13</sub>O<sub>9</sub>P
| MolarMass = 262.1535 g/mol
| CASNo = 643-13-0
| Density =
| Solubility =
| MeltingPt =
| BoilingPt =
| pKa =
| pKb =
| IsoelectricPt =
| DeltaHf =
| DeltaHc =
| EINECS =
| PubChem =
| SMILES = O1C(CO)(O)C(O)C(O)C1COP<br>(O)(O)=O
| InChI =
}}
'''Fructose 6-phosphate''' (also known as the '''Neuberg ester''') is [[fructose]] sugar [[phosphorylated]] on carbon 6 (ie. is a [[fructosephosphate]]). The β-<small>D</small>-form of this compound is very common in [[cell (biology)|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]].
==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]]).<ref>Fruton, Joseph S. ''Proteins, Enzymes, Genes: The Interplay of Chemistry and Biology''. Yale University Press: New Haven, 1999. p 292</ref>
==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]].
{{-}}
{{Biochemical Reaction
|reaction_A_major_substrate=α-<small>D</small>-[[glucose 6-phosphate]]
|reaction_A_major_substrate_image=alpha-D-glucose-6-phosphate_wpmp.png
|reaction_A_foward_enzyme=[[Phosphoglucose isomerase]]
|reaction_A_reverse_enzyme=[[Phosphoglucose isomerase]]
|reaction_A_reaction_direction_(foward/reversible/reverse)=reversible
|reaction_A_minor_reverse_product(s)=
|reaction_A_minor_reverse_substrate(s)=
|reaction_A_minor_foward_substrate(s)=
|reaction_A_minor_foward_product(s)=
|reaction_A_major_product=β-<small>D</small>-[[fructose 6-phosphate]]
|reaction_A_major_product_image=beta-D-fructose-6-phosphate_wpmp.png
|reaction_B_foward_enzyme=[[Phosphofructokinase-1]]
|reaction_B_reverse_enzyme=[[Fructose bisphosphatase]]
|reaction_B_reaction_direction_(foward/reversible/reverse)=reversible
|reaction_B_minor_foward_substrate(s)=[[adenosine triphosphate|ATP]]
|reaction_B_minor_foward_product(s)=[[ADP]]
|reaction_B_minor_reverse_product(s)=P<sub>i</sub>
|reaction_B_minor_reverse_substrate(s)=H<sub>2</sub>O
|reaction_B_major_product=β-<small>D</small>-[[fructose 1,6-bisphosphate]]
|reaction_B_major_product_image=beta-D-fructose-1,6-bisphosphate_wpmp.png
}}
{{KEGG compound|C00668}} {{KEGG enzyme|5.3.1.9}} {{KEGG compound|C05345}} {{KEGG enzyme|2.7.1.11}} {{KEGG enzyme|3.1.3.11}} {{KEGG reaction|}} {{KEGG compound|C05378}}
==Fructose 6-phosphate isomerism==
{{main|Fructose}}
Fructose 6-phosphate has only one biologically active [[isomer]], the β-<small>D</small>-form. There are many other isomers, analogous to those of fructose.
==See also==
* [[Phosphofructokinase 2]] is [[Fructose 2,6-bisphosphatase]]. This is one of the regulatory reactions of glycolysis.
* [[Mannose phosphate isomerase]] creates [[mannose-6-phosphate]].
{{Glycolysis}}
==References==
{{reflist}}
{{metabolism-stub}}
[[Category:Organophosphates]]
[[de:Fructose-6-phosphat]]
[[it:Fruttosio 6-fosfato]]
[[ja:フルクトース-6-リン酸]]
[[pt:Frutose-6-fosfato]]
[[zh:果糖-6-磷酸]]