Glucose-6-phosphate: Difference between revisions

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{| align="right" width="300" border="1" cellspacing="0" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse"
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{{Image|Glucose-6-phosphate structures.jpg|right|350px|Glucose-6-phosphate}}
| align="center" colspan="2" | [[Image:Glucose-6-phosphate-skeletal.png|120px|Glucose-6-phosphate]][[Image:Glucose-6-phosphate-3D-vdW.png|120px|Glucose-6-phosphate]] <br/> ''Glucose-6-phosphate''
'''Glucose-6-phosphate''', often abbreviated as '''G6P''', is [[glucose]] that has been [[phosphorylated]] on carbon 6. The conversion from glucose to G6P is the first step of [[glycolysis]] for energy production in [[cell (biology)|cells]].  This compound is very common in cells as the vast majority of glucose entering a cell will become phosphorylated in this way.  Like glucose, it exists in linear and cyclic forms.
|-
| align="center" colspan="2" | '''[[IUPAC nomenclature|Chemical name]]''' <br/>D-glucose-6-phosphate
|- style="border-top: 3px solid gray"
! bgcolor="#ffddaa" colspan="2" | General
|-
| bgcolor="#ffeedd" | [[Chemical formula]]
| C<sub>6</sub>H<sub>13</sub>O<sub>9</sub>P
|-
| bgcolor="#ffeedd" | [[Molecular weight]]
| 260.14 g/mol
|-
| bgcolor="#ffeedd" | Appearance
| ?
|-
| bgcolor="#ffeedd" | [[CAS number]]
| 56-73-5
|-
| bgcolor="#ffeedd" | [[MSDS]]
| [[Wikisource:Glucose-6-phosphate MSDS|Glucose-6-phosphate MSDS]]
|-
! bgcolor="#ffeedd" colspan="2" | Other names
|-
| colspan="2" |
* '''D-glucose-6-P'''
* '''glucose-6-P'''
* '''D-glucose-6-phosphate'''
|-
! bgcolor="#ffddaa" colspan="2" | Physical properties
|-
| bgcolor="#ffeedd" | [[Density]] and [[phase (matter)|phase]] at [[standard temperature and pressure|STP]]
| ?
|-
| bgcolor="#ffeedd" | [[Solubility]]
| ?
|-
| bgcolor="#ffeedd" | [[Specific gravity]]
| ?
|-
| bgcolor="#ffeedd" | [[Crystal structure]]
| ?
|-
| bgcolor="#ffeedd" | [[pH]] (10% [[solution]] with [[water]])<br/>(pKa)
| ?
|-
| bgcolor="#ffeedd" | [[Acidity constant]]<br/>(pKa)
| ?
|-
| bgcolor="#ffeedd" | Thermal decomposition
| ? K (? °C)
|-
! bgcolor="#ffddaa" colspan="2" | Phase behavior
|-
| bgcolor="#ffeedd" | [[Melting point]]
| ?
|-
| bgcolor="#ffeedd" | [[Boiling point]]
| ?
|-
| bgcolor="#ffeedd" | [[Triple point]]
| ?
|-
| bgcolor="#ffeedd" | [[Critical point]]
| ?
|-
| bgcolor="#ffeedd" | [[Heat of fusion]]<br/>(Δ<sub>fus</sub>H)
| ?
|-
| bgcolor="#ffeedd" | [[Entropy of fusion]]<br/>(Δ<sub>fus</sub>S)
| ?
|-
| bgcolor="#ffeedd" | [[Heat of vaporization]]<br/>(Δ<sub>vap</sub>H)
| ?
|-
! bgcolor="#ffddaa" colspan="2" | Safety
|-
| bgcolor="#ffeedd" | Ingestion
| ?
|-
| bgcolor="#ffeedd" | Inhalation
| ?
|-
| bgcolor="#ffeedd" | Skin
| ?
|-
| bgcolor="#ffeedd" | Eyes
| ?
|-
| bgcolor="#ffeedd" | [[Flash point]]
| ?
|-
| bgcolor="#ffeedd" | [[Autoignition temperature]]
| ?
|-
| bgcolor="#ffeedd" | [[Explosive limit]]s
| ?
|-
| bgcolor="#ffeedd" | [[OSHA]] [[Permissible Exposure Limit]]<br/>(PEL)
| ?
|-
| bgcolor="#ffeedd" | [[NIOSH]] [[Immediate Danger to Life and Health]]<br/>(IDLH)
| ?
|-
! bgcolor="#ffeedd" colspan="2" | Precautions
|-
| colspan="2" |
* '''Hazards''':
** N/A
* '''Personal protection''':
** N/A
* '''Reacts with''':
** N/A
* '''Storage''':
** N/A
|- style="border-top: 3px solid gray"
! bgcolor="#ffddaa" colspan="2" | [[Solid]] properties
|-
| bgcolor="#ffeedd" | [[Standard enthalpy change of formation]]<br/>(Δ<sub>f</sub>H<sup>0</sup><sub>solid</sub>)
| ?
|-
| bgcolor="#ffeedd" | [[Standard molar entropy]]<br/>(S<sup>0</sup><sub>solid</sub>)
| ?
|-
| bgcolor="#ffeedd" | [[Heat capacity]]<br/>(C<sub>p</sub>)
| ?
|-
! bgcolor="#ffddaa" colspan="2" | [[Liquid]] properties
|-
| bgcolor="#ffeedd" | Δ<sub>f</sub>H<sup>0</sup><sub>liquid</sub>
| ?
|-
| bgcolor="#ffeedd" | S<sup>0</sup><sub>liquid</sub>
| ?
|-
| bgcolor="#ffeedd" | C<sub>p</sub>
| ?
|-
| bgcolor="#ffeedd" | Density
| ?
|-
! bgcolor="#ffddaa" colspan="2" | [[Gas]] properties
|-
| bgcolor="#ffeedd" | Δ<sub>f</sub>H<sup>0</sup><sub>gas</sub>
| ?
|-
| bgcolor="#ffeedd" | S<sup>0</sup><sub>gas</sub>
| ?
|-
| bgcolor="#ffeedd" | C<sub>p</sub>
| ?
|- style="border-top: 3px solid gray"
| bgcolor="#ffddaa" colspan="2" align="center" |
<small>
'''Except where noted, all data was produced under conditions of [[standard temperature and pressure]].'''
</small>
|-
|}


Glucose 6-phosphate is [[glucose]] sugar [[phosphorylated]] on carbon 6. This compound is very common in [[cell (biology)|cells]] as the vast majority of glucose entering a cell will become phosphorylated in this way.
Because if its prominent position in cellular chemistry, glucose-6-phosphate has many possible fates within the cell. It lies at the start of two major [[metabolic pathway]]s, namely glycolysis and the [[pentose phosphate pathway]].  In addition to these metabolic pathways, glucose-6-phosphate may also be converted to [[glycogen]] or [[starch]] for storage. This storage is in the [[liver]] in the form of glycogen for most multicellular [[animals]], and in [[intracellular]] starch or glycogen granules for most other organisms.


Because if its prominent position in cellular chemistry, glucose 6-phosphate has many possible fates within the cell. It lies at the start of two major [[metabolic pathway]]s:
==Production of glucose-6-phosphate==
*[[Glycolysis]]
*[[Pentose phosphate pathway]]
In addition to these metabolic pathways, glucose 6-phosphate may also be converted to [[glycogen]] or [[starch]] for storage. This storage is in the [[liver]] in the form of glycogen for most multicellular [[animals]], and in [[intracellular]] starch or glycogen granules for most other organisms.


==Production of glucose 6-phosphate==
The major reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged [[phosphate]] group so that the [[glucose-6-phosphate]] cannot easily cross the [[cell membrane]], in contrast to free [[glucose]].


The major reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged [[phosphate]] group so the [[glucose 6-phosphate]] cannot easily cross the [[cell membrane]], in contrast to free [[glucose]].
Within a cell, glucose-6-phosphate is produced by phosphorylation of glucose on the sixth carbon. This is catalyzed by the [[enzyme]] [[hexokinase]] in most cells, and [[glucokinase]] in certain cells, most notably liver cells. One [[adenosine triphosphate|ATP]] is consumed in this reaction.  


Within a cell, glucose 6-phosphate is produced by phosphorylation of [[glucose]] on the sixth carbon. This is catalyzed by the [[enzyme]] [[hexokinase]] in most cells, and [[glucokinase]] in certain cells, most notably liver cells. One [[Adenosine triphosphate|ATP]] is consumed in this reaction.
<!--{{Enzymatic Reaction
 
{{Enzymatic Reaction
|foward_enzyme=[[Hexokinase]]
|foward_enzyme=[[Hexokinase]]
|reverse_enzyme=
|reverse_enzyme=
|substrate=α-<small>D</small>-[[Glucose]]
|substrate=α-<small>D</small>-[[Glucose]]
|product=α-<small>D</small>-[[Glucose 6-phosphate]]
|product=α-<small>D</small>-[[Glucose-6-phosphate]]
|reaction_direction_(foward/reversible/reverse)=foward
|reaction_direction_(foward/reversible/reverse)=foward
|minor_foward_substrate(s)=[[ATP]]
|minor_foward_substrate(s)=[[ATP]]
Line 185: Line 24:
|product_image=Glucose-6-phosphate_wpmp.png
|product_image=Glucose-6-phosphate_wpmp.png
}}
}}
{{KEGG compound|C00031}} {{KEGG enzyme|2.7.1.1}} {{KEGG compound|C00668}} {{KEGG reaction|R01786}}
{{KEGG compound|C00031}} {{KEGG enzyme|2.7.1.1}} {{KEGG compound|C00668}} {{KEGG reaction|R01786}}-->


Glucose-6-phosphate is also produced during [[glycogenolysis]] from glucose-1-phosphate, the first product of the breakdown of [[glycogen]] polymers.
Glucose-6-phosphate is also produced during [[glycogenolysis]] from [[glucose-1-phosphate]], the first product of the breakdown of [[glycogen]] polymers.


== Fate 1: Pentose Phosphate Pathway ==
== Fate 1: Pentose phosphate pathway ==
When the ratio of NADP<sup>+</sup> : NADPH increases, the body realizes it needs to produce more NADPH (a reducing agent for several reactions like fatty acid synthesis).  This will cause the G6P to be dehydrogenated by glucose 6-phosphate dehydrogenase.  This reversible reaction is the initial step of the [[pentose phosphate pathway]], which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules .  Also, if the body needs nucleotide precursors of DNA for growth and synthesis, G6P  will also be dehydrogenated and enter the pentose phosphate pathway.
When the ratio of NADP<sup>+</sup> : [[NADPH]] increases, the body realizes it needs to produce more NADPH (a reducing agent for several reactions like fatty acid synthesis).  This will cause the G6P to be dehydrogenated by [[glucose-6-phosphate dehydrogenase]].  This reversible reaction is the initial step of the [[pentose phosphate pathway]], which generates the useful cofactor NADPH as well as [[ribulose-5-phosphate]], a carbon source for the synthesis of other molecules .  Also, if the body needs nucleotide precursors of DNA for growth and synthesis, G6P  will also be dehydrogenated and enter the pentose phosphate pathway.


== Fate 2: Glycolysis ==
== Fate 2: Glycolysis ==
If the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for [[glycolysis]]. Glucose 6-phosphate is first isomerized to [[fructose-6-phosphate]] by [[phosphoglucose isomerase]]
{{Image|G6P to F6P reaction.jpg|right|400px|Conversion of G6P to F6P}}
 
If the cell needs energy or carbon skeletons for synthesis then glucose-6-phosphate is targeted for [[glycolysis]]. G6P (an [[aldose]]) is first isomerized to [[fructose-6-phosphate]] (F6P, a [[ketose]]) by the enzyme [[phosphoglucose isomerase]] F6P exists in both the open chain form and cyclic forms.
{{Enzymatic Reaction
|foward_enzyme=[[Phosphoglucose isomerase]]
|reverse_enzyme=[[Phosphoglucose isomerase]]
|substrate=α-<small>D</small>-[[Glucose 6-phosphate]]
|product=β-<small>D</small>-[[Fructose 6-phosphate]]
|reaction_direction_(foward/reversible/reverse)=reversible
|minor_foward_substrate(s)=
|minor_foward_product(s)=
|minor_reverse_substrate(s)=
|minor_reverse_product(s)=
|substrate_image=Glucose-6-phosphate_wpmp.png
|product_image=Fructose-6-phosphate_wpmp.png
}}
{{KEGG compound|C00668}} {{KEGG enzyme|5.3.1.9}} {{KEGG compound|C05345}} {{KEGG reaction|R00771}}


This reaction converts glucose 6-phosphate to [[fructose 6-phosphate]] in preparation for phosphorylation to [[Fructose-1,6-bisphosphate]].  The addition of the 2<sup>nd</sup> phosphoryl group to produce Fructose-1,6-bisphosphate is an irreversible step, and so is used to irreversibly target the glucose 6-phosphate breakdown to provide energy for ATP production via [[glycolysis]].
This reaction converts glucose-6-phosphate to fructose-6-phosphate in preparation for phosphorylation to [[fructose-1,6-bisphosphate]] by the enzyme [[phosphofructokinase]].  The addition of the second phosphate group to produce fructose-1,6-bisphosphate is an irreversible step, and so is used to irreversibly target the glucose-6-phosphate breakdown to provide energy for ATP production via glycolysis.


== Fate 3: Storage as Glycogen ==
== Fate 3: Storage as glycogen ==


Whenever cellular glucose-6-phosphate levels are high the [[osmotic pressure]] inside the cells increases, and this may lead water to diffuse into the cell, causing it to become turgid and (eventually) lyse. Since osmotic pressure is proportional to the concentration of solutes, rather than to the total mass of solutes, this problem can be overcome by storing glucose-6-P in a polymeric form. In plant cells, this polymeric form of glucose is [[starch]], whereas animals store [[glycogen]].
Whenever cellular glucose-6-phosphate levels are high the [[osmotic pressure]] inside the cell increases, and this may lead water to diffuse into the cell, causing it to become turgid and (eventually) lyse. Since osmotic pressure is proportional to the concentration of solutes, rather than to the total mass of solutes, this problem can be overcome by storing G6P in a polymeric form. In plant cells, this polymeric form of glucose is [[starch]], whereas animals store [[glycogen]].


== Fate 4: Dephosphorylation and Release into Bloodstream ==
== Fate 4: Dephosphorylation and release into the bloodstream ==
Liver cells possess [[glucose-6-phosphatase]], which removes the phosphate group from glucose-6-phosphate produced during [[glycogenolysis]] or [[gluconeogenesis]]. The free glucose is sent into the bloodstream for uptake by other cells.
Liver cells possess [[glucose-6-phosphatase]], which removes the phosphate group from glucose-6-phosphate produced during [[glycogenolysis]] or [[gluconeogenesis]]. The free glucose is sent into the bloodstream for uptake by other cells.


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* {{cite book |last=Berg |first=Jeremy M. |coauthors=Tymoczko, Stryer |title=Biochemistry |year=2002 |edition=5th |publisher=[[W.H. Freeman and Company]] |location=New York |id=ISBN 0-7167-3051-0 | url =http://www.ncbi.nlm.nih.gov/books/bv.fcgi?call=bv.View..ShowTOC&rid=stryer.TOC&depth=10}}
* {{cite book |last=Berg |first=Jeremy M. |coauthors=Tymoczko, Stryer |title=Biochemistry |year=2002 |edition=5th |publisher=[[W.H. Freeman and Company]] |location=New York |id=ISBN 0-7167-3051-0 | url =http://www.ncbi.nlm.nih.gov/books/bv.fcgi?call=bv.View..ShowTOC&rid=stryer.TOC&depth=10}}
==See also==
* [[Glucose]]
* [[Glycogen]]
* [[Glucose 1-phosphate]]
* [[Pentose phosphate pathway]]
* [[Starch]]
[[Category:Organophosphates]]
[[Category:Monosaccharides]]
[[Category:CZ Live]]

Latest revision as of 22:41, 1 February 2009

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(CC) Image: David E. Volk
Glucose-6-phosphate

Glucose-6-phosphate, often abbreviated as G6P, is glucose that has been phosphorylated on carbon 6. The conversion from glucose to G6P is the first step of glycolysis for energy production in cells. This compound is very common in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. Like glucose, it exists in linear and cyclic forms.

Because if its prominent position in cellular chemistry, glucose-6-phosphate has many possible fates within the cell. It lies at the start of two major metabolic pathways, namely glycolysis and the pentose phosphate pathway. In addition to these metabolic pathways, glucose-6-phosphate may also be converted to glycogen or starch for storage. This storage is in the liver in the form of glycogen for most multicellular animals, and in intracellular starch or glycogen granules for most other organisms.

Production of glucose-6-phosphate

The major reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so that the glucose-6-phosphate cannot easily cross the cell membrane, in contrast to free glucose.

Within a cell, glucose-6-phosphate is produced by phosphorylation of glucose on the sixth carbon. This is catalyzed by the enzyme hexokinase in most cells, and glucokinase in certain cells, most notably liver cells. One ATP is consumed in this reaction.


Glucose-6-phosphate is also produced during glycogenolysis from glucose-1-phosphate, the first product of the breakdown of glycogen polymers.

Fate 1: Pentose phosphate pathway

When the ratio of NADP+ : NADPH increases, the body realizes it needs to produce more NADPH (a reducing agent for several reactions like fatty acid synthesis). This will cause the G6P to be dehydrogenated by glucose-6-phosphate dehydrogenase. This reversible reaction is the initial step of the pentose phosphate pathway, which generates the useful cofactor NADPH as well as ribulose-5-phosphate, a carbon source for the synthesis of other molecules . Also, if the body needs nucleotide precursors of DNA for growth and synthesis, G6P will also be dehydrogenated and enter the pentose phosphate pathway.

Fate 2: Glycolysis

(CC) Image: David E. Volk
Conversion of G6P to F6P

If the cell needs energy or carbon skeletons for synthesis then glucose-6-phosphate is targeted for glycolysis. G6P (an aldose) is first isomerized to fructose-6-phosphate (F6P, a ketose) by the enzyme phosphoglucose isomerase F6P exists in both the open chain form and cyclic forms.

This reaction converts glucose-6-phosphate to fructose-6-phosphate in preparation for phosphorylation to fructose-1,6-bisphosphate by the enzyme phosphofructokinase. The addition of the second phosphate group to produce fructose-1,6-bisphosphate is an irreversible step, and so is used to irreversibly target the glucose-6-phosphate breakdown to provide energy for ATP production via glycolysis.

Fate 3: Storage as glycogen

Whenever cellular glucose-6-phosphate levels are high the osmotic pressure inside the cell increases, and this may lead water to diffuse into the cell, causing it to become turgid and (eventually) lyse. Since osmotic pressure is proportional to the concentration of solutes, rather than to the total mass of solutes, this problem can be overcome by storing G6P in a polymeric form. In plant cells, this polymeric form of glucose is starch, whereas animals store glycogen.

Fate 4: Dephosphorylation and release into the bloodstream

Liver cells possess glucose-6-phosphatase, which removes the phosphate group from glucose-6-phosphate produced during glycogenolysis or gluconeogenesis. The free glucose is sent into the bloodstream for uptake by other cells.

References