Fructose 1,6-bisphosphate

Fructose 1,6-bisphosphate
Names
	IUPAC name 1,6-Di-O-phosphono-β-D-fructofuranose
Identifiers
CAS Number	488-69-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:32966 ;
ChEMBL	ChEMBL1089962 ;
ChemSpider	9848 ;
ECHA InfoCard	100.006.985
KEGG	C00354;
MeSH	fructose-1,6-diphosphate
PubChem CID	10267;
UNII	M7522JYX1H ;
CompTox Dashboard (EPA)	DTXSID0048347 ;
	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 Key: RNBGYGVWRKECFJ-ARQDHWQXSA-N ; 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-ARQDHWQXSA;
	SMILES C([C@@H]1[C@H]([C@@H]([C@](O1)(COP(=O)(O)O)O)O)O)OP(=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). verify (what is ?) Infobox references

Fructose 1,6-bisphosphate, known in older publications 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 common in cells.^[1] Upon entering the cell, most glucose and fructose is converted to fructose 1,6-bisphosphate.^[2]^[3]

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 ^[4]

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

	Fructose 1,6-bisphosphatase			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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|alt=Glycolysis and Gluconeogenesis edit]]

Glycolysis and Gluconeogenesis edit

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

Isomerism

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.^[5]

References

^ Alfarouk, Khalid O.; Verduzco, Daniel; Rauch, Cyril; Muddathir, Abdel Khalig; Bashir, Adil H. H.; Elhassan, Gamal O.; Ibrahim, Muntaser E.; Orozco, Julian David Polo; Cardone, Rosa Angela; Reshkin, Stephan J.; Harguindey, Salvador (18 December 2014). "Glycolysis, tumor metabolism, cancer growth and dissemination. A new pH-based etiopathogenic perspective and therapeutic approach to an old cancer question". Oncoscience. 1 (12): 777–802. doi:10.18632/oncoscience.109. PMC 4303887. PMID 25621294.
^ 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.
^ Ishwar, Arjun (2015). "Distinguishing the Interactions in the Fructose 1,6-Bisphosphate Binding Site of Human Liver Pyruvate Kinase That Contribute to Allostery". Biochemistry. 54 (7): 1516–1524. doi:10.1021/bi501426w. PMC 5286843. PMID 25629396.
^ 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 (3): 416–420. doi:10.1016/j.carres.2010.12.008. PMID 21232735.

External links

Media related to Fructose 1,6-bisphosphate at Wikimedia Commons

[WikiPathways-5] The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".

[1] Alfarouk, Khalid O.; Verduzco, Daniel; Rauch, Cyril; Muddathir, Abdel Khalig; Bashir, Adil H. H.; Elhassan, Gamal O.; Ibrahim, Muntaser E.; Orozco, Julian David Polo; Cardone, Rosa Angela; Reshkin, Stephan J.; Harguindey, Salvador (18 December 2014). "Glycolysis, tumor metabolism, cancer growth and dissemination. A new pH-based etiopathogenic perspective and therapeutic approach to an old cancer question". Oncoscience. 1 (12): 777–802. doi:10.18632/oncoscience.109. PMC 4303887. PMID 25621294.

[2] Berg, Jeremy M.; Tymoczko, Stryer (2002). Biochemistry (5th ed.). New York: W.H. Freeman and Company. ISBN 0-7167-3051-0.

[3] Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.

[4] Ishwar, Arjun (2015). "Distinguishing the Interactions in the Fructose 1,6-Bisphosphate Binding Site of Human Liver Pyruvate Kinase That Contribute to Allostery". Biochemistry. 54 (7): 1516–1524. doi:10.1021/bi501426w. PMC 5286843. PMID 25629396.

[6] 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 (3): 416–420. doi:10.1016/j.carres.2010.12.008. PMID 21232735.

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