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Fructose 6-phosphate

Names
IUPAC name 6-O-Phosphono-α-D-fructofuranose
Other names β-D-fructose 6-phosphate, fructose 6-phosphate
Identifiers
CAS Number	643-13-0
3D model (JSmol)	Interactive image
Abbreviations	F6P
ChEBI	CHEBI:16084
ChemSpider	392657
ECHA InfoCard	100.010.360
KEGG	C00085
PubChem CID	444848
UNII	2012QM764Y
CompTox Dashboard (EPA)	DTXSID80904350
InChI InChI=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/s1Key: BGWGXPAPYGQALX-ZXXMMSQZSA-N 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/s1Key: BGWGXPAPYGQALX-ZXXMMSQZBI
SMILES O=P(O)(O)OC1O(O)(CO)(O)1O
Properties
Chemical formula	C6H13O9P
Molar mass	260.14 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

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. 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.

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		α-D-fructose 6-phosphate	Phosphofructokinase-1		α-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 at KEGG Pathway Database. Compound C05378 at KEGG Pathway Database.

Click on genes, proteins and metabolites below to link to respective articles.

1. The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

See also

• Mannose phosphate isomerase

v t e Glycolysis metabolic pathway

Glucose Hexokinase ATP ADP Glucose 6-phosphate Glucose-6-phosphate isomerase Fructose 6-phosphate Phosphofructokinase-1 ATP ADP Fructose 1,6-bisphosphate Fructose-bisphosphate aldolase Dihydroxyacetone phosphate + + Glyceraldehyde 3-phosphate Triosephosphate isomerase 2 × Glyceraldehyde 3-phosphate 2 ×  Glyceraldehyde-3-phosphate dehydrogenase NAD+ Pi NADH + H NAD+ Pi NADH + H 2 × 1,3-Bisphosphoglycerate 2 ×  Phosphoglycerate kinase ADP ATP ADP ATP 2 × 3-Phosphoglycerate 2 ×  Phosphoglycerate mutase 2 × 2-Phosphoglycerate 2 ×  Phosphopyruvate hydratase (enolase)   H2O   H2O 2 × Phosphoenolpyruvate 2 ×  Pyruvate kinase ADP ATP 2 × Pyruvate 2 ×

References

1. Berg, Jeremy M.; Tymoczko, Stryer (2002). Biochemistry (5th ed.). New York: W.H. Freeman and Company. ISBN 0-7167-3051-0.
2. Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
3. Fruton, Joseph S. Proteins, Enzymes, Genes: The Interplay of Chemistry and Biology. Yale University Press: New Haven, 1999. p 292

• Monosaccharide derivatives
• Organophosphates
• Pentose phosphate pathway
• Phosphate esters
• Glycolysis