View source for Fructose 6-phosphate

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470454308
| ImageFile = beta-D-fructose-6-phosphate_wpmp.png
| ImageClass = skin-invert
| ImageFile2= Fructose 6-phosphate.png
| ImageSize = 150px
| IUPACName = 6-''O''-Phosphono-α-<small>D</small>-fructofuranose
| OtherNames = β-D-fructose 6-phosphate, <br>fructose 6-phosphate
| Section1 = {{Chembox Identifiers
|   Abbreviations = F6P
|   EINECS = 
|   PubChem = 444848
|   KEGG = C00085
|   SMILES = O=P(O)(O)OC[C@H]1O[C@@](O)(CO)[C@@H](O)[C@@H]1O
|   ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 392657
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 16084
| InChIKey = BGWGXPAPYGQALX-ZXXMMSQZBI
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BGWGXPAPYGQALX-ZXXMMSQZSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 643-13-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2012QM764Y
|   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
}}
| Section2 = {{Chembox Properties
|   Formula = C<sub>6</sub>H<sub>13</sub>O<sub>9</sub>P
|   MolarMass = 260.14 g/mol
|   Density = 
|   Solubility = 
|   MeltingPt = 
|   BoilingPt = 
|   pKa = 
|   pKb = 
|   IsoelectricPt = 
}}
}}

'''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 [[fructosephosphate]]s. The β-<small>D</small>-form of this compound is very common in [[cell (biology)|cells]].<ref>{{cite book |last=Berg |first=Jeremy M. |author2=Tymoczko, Stryer |title=Biochemistry |year=2002 |edition=5th |publisher=[[W.H. Freeman and Company]] |location=New York |isbn=0-7167-3051-0 |url=https://archive.org/details/biochemistrychap00jere |url-access=registration }}</ref><ref>Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. {{ISBN|1-57259-153-6}}.</ref> 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.

==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]].<ref>Fruton, Joseph S.  ''Proteins, Enzymes, Genes: The Interplay of Chemistry and Biology''.  Yale University Press: New Haven, 1999. p 292</ref>

==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]]. 
{| style="background: white; text-align:center;"
|-
| style="background:lightgreen" | α-{{small|D}}-[[glucose 6-phosphate]]
| colspan="2" style="background:pink; width:75px" | [[Phosphoglucose isomerase]]
| style="background:lightgreen" | α-{{small|D}}-fructose 6-phosphate
| colspan="2" style="background:pink; width:75px" | [[Phosphofructokinase-1]]
| style="background:lightgreen" | α-{{small|D}}-[[fructose 1,6-bisphosphate]]
|-
| rowspan="5" | [[image:alpha-D-glucose-6-phosphate_wpmp.png]]
| colspan="2" style="width:75px" | &nbsp;
| rowspan="5" | [[image:beta-D-fructose-6-phosphate_wpmp.png]]
| colspan="2" style="width:75px" | &nbsp;
| rowspan="5" | [[image:beta-D-fructose-1,6-bisphosphate_wpmp.png]]
|-
| 
| 
| [[adenosine triphosphate|ATP]]
| [[Adenosine diphosphate|ADP]]
|-
| colspan="2" style="width:75px" | [[image:Biochem_reaction_arrow_reversible_NNNN_horiz_med.svg|75px]]
| colspan="2" style="width:75px" | [[image:Biochem_reaction_arrow_reversible_YYYY_horiz_med.svg|75px]]
|-
| 
| 
| P<sub>i</sub>
| H<sub>2</sub>O
|-
| colspan="2" style="width:75px" | &nbsp;
| colspan="2" style="width:75px" | &nbsp;
|-
| &nbsp;
| colspan="2" style="background:pink; width:75px" | [[Phosphoglucose isomerase]]
| &nbsp;
| colspan="2" style="background:pink; width:75px" | [[Fructose 1,6-bisphosphatase|Fructose bisphosphatase]]
| align="right" |
|}
{{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}}

{{GlycolysisGluconeogenesis_WP534|highlight=Fructose_6-phosphate}}


==See also==
* [[Mannose phosphate isomerase]]

{{Glycolysis}}

==References==
{{reflist}}

{{DEFAULTSORT:Fructosephosphate6}}
[[Category:Monosaccharide derivatives]]
[[Category:Organophosphates]]
[[Category:Pentose phosphate pathway]]
[[Category:Phosphate esters]]
[[Category:Glycolysis]]