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-D-fructofuranose

| OtherNames = β-D-fructose 6-phosphate,
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

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| Section2 = {{Chembox Properties

| Formula = C6H13O9P

| MolarMass = 260.14 g/mol

| Density =

| Solubility =

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| BoilingPt =

| pKa =

| pKb =

| IsoelectricPt =

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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 fructosephosphates. The β-D-form of this compound is very common in cells.{{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 }}Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. {{ISBN|1-57259-153-6}}. 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.Fruton, Joseph S. Proteins, Enzymes, Genes: The Interplay of Chemistry and Biology. Yale University Press: New Haven, 1999. p 292

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" |  

| rowspan="5" | image:beta-D-fructose-6-phosphate_wpmp.png

| colspan="2" style="width:75px" |  

| rowspan="5" | image:beta-D-fructose-1,6-bisphosphate_wpmp.png

|

| ATP

| ADP

colspan="2" style="width:75px" | 75px

| colspan="2" style="width:75px" | 75px

|

| Pi

| H2O

colspan="2" style="width:75px" |  

| colspan="2" style="width:75px" |  

 

| colspan="2" style="background:pink; width:75px" | Phosphoglucose isomerase

|  

| colspan="2" style="background:pink; width:75px" | 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

References