Fructose 6-phosphate

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^Y
3D model (JSmol)	Interactive image
Abbreviations	F6P
ChEBI	CHEBI:16084^N
ChemSpider	392657^Y
ECHA InfoCard	100.010.360
KEGG	C00085
PubChem CID	444848
UNII	2012QM764Y^Y
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/s1^Y Key: BGWGXPAPYGQALX-ZXXMMSQZSA-N^Y 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 Key: BGWGXPAPYGQALX-ZXXMMSQZBI
SMILES O=P(O)(O)OC[C@H]1O[C@@](O)(CO)[C@@H](O)[C@@H]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 [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

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.^[1]^[2] 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.^[3]

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

			P_i	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 [1] at KEGG Pathway Database. Compound C05378 at KEGG Pathway Database.

Click on genes, proteins and metabolites below to link to respective articles.^{[§ 1]}

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|alt=Glycolysis and Gluconeogenesis edit]]

Glycolysis and Gluconeogenesis edit

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

References

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