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'''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-<small>D</small>-form of this compound is common in [[cell (biology)|cells]]. Upon entering the cell, most [[glucose]] and fructose is converted to fructose 1,6-bisphosphate.<ref>{{cite book |last=Berg |first=Jeremy M. |author2=Tymoczko, Stryer |title=Biochemistry |year=2002 |edition=5th |publisher=[[W.H. Freeman and Company]] |location=New York |isbn=0-7167-3051-0 | url =https://www.ncbi.nlm.nih.gov/books/bv.fcgi?call=bv.View..ShowTOC&rid=stryer.TOC&depth=10}}</ref><ref>Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. {{ISBN|1-57259-153-6}}.</ref> |
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==In glycolysis== |
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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 <ref>{{cite journal|doi=10.1021/bi501426w | volume=54 | title=Distinguishing the Interactions in the Fructose 1,6-Bisphosphate Binding Site of Human Liver Pyruvate Kinase That Contribute to Allostery | journal=Biochemistry | pages=1516–1524 | last1 = Ishwar | first1 = Arjun| pmc=5286843 }}</ref> |
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<div style="overflow:auto; border:1px #aaa solid; clear:both"> |
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{| style="background:white; text-align:center;" |
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|- |
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| style="background:lightgreen" | β-{{small|D}}-[[fructose 6-phosphate]] |
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| colspan="2" style="background:pink" | [[Phosphofructokinase 1|6-phosphofructo-1-kinase]] |
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| style="background:lightgreen" | β-{{small|D}}-fructose 1,6-bisphosphate |
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| colspan="2" style="background:pink" | [[Fructose-bisphosphate aldolase]] |
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| style="background:lightgreen" | {{small|D}}-[[glyceraldehyde 3-phosphate]] |
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| style="background:lightgreen" | |
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| style="background:lightgreen" |[[dihydroxyacetone phosphate]] |
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|- |
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| rowspan="5" | [[image:beta-D-fructose-6-phosphate wpmp.png]] |
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| colspan="2" | |
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| rowspan="5" | [[image:beta-D-fructose-1,6-bisphosphate wpmp.png]] |
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| colspan="2" | |
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| rowspan="5" | [[image:D-glyceraldehyde-3-phosphate wpmp.png]] |
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| rowspan="5" width="25" | <span style="font-size:140%;">'''+'''</span> |
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| rowspan="5" | [[image:glycerone-phosphate wpmp.png]] |
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|- |
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| [[adenosine triphosphate|ATP]] |
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| [[Adenosine diphosphate|ADP]] |
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| colspan="2" | [[image:Biochem reaction arrow reversible YYYY horiz med.svg]] |
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| colspan="2" | [[image:Biochem reaction arrow reversible NNNN horiz med.svg]] |
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|- |
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| P<sub>i</sub> |
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| H<sub>2</sub>O |
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| colspan="2" | |
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| colspan="2" | |
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|- |
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| align="left"| |
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| colspan="2" style="background:pink" | [[Fructose 1,6-bisphosphatase]] |
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| align="right" | |
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| colspan="2" style="background:pink" | [[Fructose-bisphosphate aldolase]] |
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</div> |
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{{KEGG compound|C05345}} {{KEGG enzyme|2.7.1.11}} {{KEGG enzyme|3.1.3.11}} {{KEGG compound|C05378}} {{KEGG enzyme|4.1.2.13}} {{KEGG compound|C00111}} {{KEGG compound|C00118}} |
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''The numbering of the carbon atoms indicates the fate of the carbons according to their position in fructose 6-phosphate.'' |
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{{GlycolysisGluconeogenesis_WP534|highlight=Fructose_1,6-bisphosphate}} |
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==Isomerism== |
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{{Main|Fructose}} |
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Fructose 1,6-bisphosphate has only one biologically active [[isomer]], the β-<small>D</small>-form. There are many other isomers, analogous to those of fructose. |
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==Iron chelation== |
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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|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 disease|Alzheimer's]] and [[Parkinson's disease|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.<ref>{{cite journal|last=Bajic|first=Aleksandar|author2=Zakrzewska J |author3=Godjevac D |author4=Andjus P |author5=Jones DR |author6=Spasic M |author7=Spasojevic I |title=Relevance of the ability of fructose 1,6-bis(phosphate) to sequester ferrous but not ferric ions|journal=Carbohydrate Research|year=2011|volume=346|pages=416–420 |doi=10.1016/j.carres.2010.12.008}}</ref> |
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==See also== |
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* [[Fructose 2,6-bisphosphate]] |
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{{Glycolysis}} |
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==References== |
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{{Reflist}} |
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{{DEFAULTSORT:Fructosebisphosphate16}} |
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[[Category:Monosaccharide derivatives]] |
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[[Category:Organophosphates]] |
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2018년 7월 2일 (월) 17:05 판
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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 common in cells. Upon entering the cell, most glucose and fructose is converted to fructose 1,6-bisphosphate.[1][2]
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 [3]
| β-D-fructose 6-phosphate | 6-phosphofructo-1-kinase | β-D-fructose 1,6-bisphosphate | Fructose-bisphosphate aldolase | D-glyceraldehyde 3-phosphate | dihydroxyacetone phosphate | |||
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+ | 
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| ATP | ADP | |||||||
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| Pi | H2O | |||||||
| Fructose 1,6-bisphosphatase | Fructose-bisphosphate aldolase | |||||||
틀:KEGG compound 틀:KEGG enzyme 틀:KEGG enzyme 틀:KEGG compound 틀:KEGG enzyme 틀:KEGG compound 틀:KEGG compound
The numbering of the carbon atoms indicates the fate of the carbons according to their position in fructose 6-phosphate.
틀:GlycolysisGluconeogenesis WP534
Isomerism
이 부분의 본문은 Fructose입니다.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.[4]
See also
References
- ↑ Berg, Jeremy M.; Tymoczko, Stryer (2002). 《Biochemistry》 5판. 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. “Distinguishing the Interactions in the Fructose 1,6-Bisphosphate Binding Site of Human Liver Pyruvate Kinase That Contribute to Allostery”. 《Biochemistry》 54: 1516–1524. doi:10.1021/bi501426w. PMC 5286843.
- ↑ 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.