Fructose 6-phosphate.html



Fructose 6-phosphate
IUPAC name	[(2R,3R,4S)-3,4,5-trihydroxy-5- (hydroxymethyl)oxolan-2-yl] methoxyphosphonic acid
Other names	β-D-fructose 6-phosphate, fructose 6-phosphate
Abbreviations	F6P
Molecular formula	C6H13O9P
Molar mass	262.1535 g/mol
CAS number	643-13-0
SMILES	O1C(CO)(O)C(O)C(O)C1COP (O)(O)=O
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

Fructose 6-phosphate (also known as the Neuberg ester) is fructose sugar phosphorylated on carbon 6 (ie. is a fructosephosphate). The β-D-form of this compound is very common in 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).¹

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.

α-D-glucose 6-phosphate	Phosphoglucose isomerase		β-D-fructose 6-phosphate	Phosphofructokinase-1		β-D-fructose 1,6-bisphosphate
				ATP	ADP
	File:Biochem reaction arrow reversible NNNN horiz med.svg
				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 [1] at KEGG Pathway Database. Compound C05378 at KEGG Pathway Database.

Fructose 6-phosphate isomerism

Main article: Fructose

Fructose 6-phosphate has only one biologically active isomer, the β-D-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.

v • d • e  Glycolysis Metabolic Pathway

Glucose Hexokinase Glucose-6-phosphate Glucose-6-phosphate isomerase Fructose 6-phosphate 6-phosphofructokinase Fructose 1,6-bisphosphate Fructose bisphosphate aldolase ATP ADP ATP ADP Dihydroxyacetone phosphate Glyceraldehyde 3-phosphate Triosephosphate isomerase Glyceraldehyde 3-phosphate Glyceraldehyde-3-phosphate dehydrogenase 1,3-Bisphosphoglycerate Phosphoglycerate kinase NAD+ + Pi NADH + H+ ADP ATP + 2 2 3-Phosphoglycerate Phosphoglycerate mutase 2-Phosphoglycerate Phosphopyruvate hydratase(Enolase) Phosphoenolpyruvate Pyruvate kinase Pyruvate Pyruvate dehydrogenase Acetyl-CoA H2O ADP ATP CoA + NAD+ NADH + H+ + CO2 2 2 2 2 2

References

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