Fructose 1,6-bisphosphate

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Fructose 1,6-bisphosphate
Beta-D-fructose-1,6-bisphosphate wpmp.png
Identifiers
CAS number 488-69-7 YesY
PubChem 445557
ChemSpider 393165 YesY
MeSH fructose-1,6-diphosphate
ChEBI CHEBI:40595 YesY
ChEMBL CHEMBL1089962 YesY
ATC code C01EB07
Jmol-3D images Image 1
Properties
Molecular formula C6H14O12P2
Molar mass 340.116
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Fructose 1,6-bisphosphate, also known as Harden-Young ester, is fructose sugar phosphorylated on carbons 1 and 6 (i.e., 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 fructose 1,6-bisphosphate at some point.

Fructose 1,6-bisphosphate in glycolysis[edit]

Fructose 1,6-bisphosphate lies within the glycolysis metabolic pathway and is produced by phosphorylation of fructose 6-phosphate. It is, in turn, broken down into two compounds: glyceraldehyde 3-phosphate and dihydroxyacetone phosphate. It is an allosteric activator of pyruvate kinase.

β-D-fructose 6-phosphate 6-phosphofructo 1-kinase β-D-fructose 1,6-bisphosphate Fructose-bisphosphate aldolase D-glyceraldehyde 3-phosphate dihydroxyacetone phosphate
Beta-D-fructose-6-phosphate wpmp.png Beta-D-fructose-1,6-bisphosphate wpmp.png D-glyceraldehyde-3-phosphate wpmp.png + Glycerone-phosphate wpmp.png
ATP ADP
Biochem reaction arrow reversible YYYY horiz med.png Biochem reaction arrow reversible NNNN horiz med.png
Pi H2O
Hexose diphosphatase Fructose-bisphosphate aldolase

Compound C05345 at KEGG Pathway Database. Enzyme 2.7.1.11 at KEGG Pathway Database. Enzyme 3.1.3.11 at KEGG Pathway Database. Compound C05378 at KEGG Pathway Database. Enzyme 4.1.2.13 at KEGG Pathway Database. Compound C00111 at KEGG Pathway Database. Compound C00118 at KEGG Pathway Database.

The numbering of the carbon atoms indicates the fate of the carbons according to their position in fructose 6-phosphate.

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

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Glycolysis and Gluconeogenesis edit
  1. ^ The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534". 

Fructose 1,6-bisphosphate isomerism[edit]

Main article: Fructose

Fructose 1,6-bisphosphate has only one biologically active isomer, the β-D-form. There are many other isomers, analogous to those of fructose.

Iron Chelation[edit]

Fructose 1,6-bis(phosphate) has also been implicated in the ability to bind and sequester Fe(II), a soluble form of iron whose oxidation to the insoluble Fe(III) is capable of generating reactive oxygen species via Fenton chemistry. The ability of fructose 1,6-bis(phosphate) to bind Fe(II) may prevent such electron transfers, and thus act as an antioxidant within the body. Certain neurodegenerative diseases, like Alzheimer's and Parkinson's, have been linked to metal deposits with high iron content, although it is uncertain whether Fenton chemistry plays a substantial role in these diseases, or whether fructose 1,6-bis(phosphate) is capable of mitigating those effects.[1]

See also[edit]


References[edit]

  1. ^ Bajic, Aleksandar; Zakrzewska J; Godjevac D; Andjus P; Jones DR; Spasic M; Spasojevic I (2011). "Relevance of the ability of fructose 1,6-bis(phosphate) to sequester ferrous but not ferric ions". Carbohydrate Research 346: 416–420. doi:10.1016/j.carres.2010.12.008.