Fructose 1,6-bisphosphate

Fructose 1,6-bisphosphate
Identifiers

CAS Number	488-69-7^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:40595^Y
ChEMBL	ChEMBL1089962^Y
ChemSpider	393165^Y
ECHA InfoCard	100.006.985
MeSH	fructose-1,6-diphosphate
PubChem	445557
InChI InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1^Y Key: RNBGYGVWRKECFJ-ZXXMMSQZSA-N^Y InChI=1/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1 Key: RNBGYGVWRKECFJ-ZXXMMSQZBN
SMILES O=P(OC[C@]1(O)O[C@@H]([C@@H](O)[C@@H]1O)COP(=O)(O)O)(O)O
Properties
Chemical formula	C₆H₁₄O₁₂P₂
Molar mass	340.116
Pharmacology
ATC code	C01EB07 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is ^YN ?)
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

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 through distinct interactions of binding and allostery at the enzyme's catalytic site ^[1]

β-D-fructose 6-phosphate	6-phosphofructo 1-kinase		β-D-fructose 1,6-bisphosphate	Fructose-bisphosphate aldolase	D-glyceraldehyde 3-phosphate		dihydroxyacetone phosphate
						+
	ATP	ADP

	P_i	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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|{{{bSize}}}px|alt=Glycolysis and Gluconeogenesis edit]]

Glycolysis and Gluconeogenesis edit

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

Fructose 1,6-bisphosphate isomerism

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

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.^[2]

References

↑ http://pubs.acs.org/doi/abs/10.1021/bi501426w
↑ 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.

This article is issued from Wikipedia - version of the 2/16/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.

Fructose 1,6-bisphosphate

Fructose 1,6-bisphosphate in glycolysis

Fructose 1,6-bisphosphate isomerism

Iron Chelation

See also

References