Misplaced Pages

Glucose 1-phosphate: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editContent deleted Content addedVisualWikitext
Revision as of 08:50, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit Latest revision as of 01:26, 3 December 2023 edit undo213.230.114.155 (talk) Last name has to be capitalized 
(34 intermediate revisions by 23 users not shown)
Line 1: Line 1:
{{unreferenced|date=June 2010}}
{{chembox {{chembox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 396144629 | verifiedrevid = 443837963
| ImageFile = Glucose 1-phosphate.svg | ImageFile = Glucose 1-phosphate.svg
| ImageSize = 150px | ImageSize = 150px
| ImageCaption = Anionic form of α-<small>D</small>-glucose 1-phosphate
| ImageFile2 = Cori ester.gif | ImageFile2 =Cori_ester.png
| ImageSize2 = 150px | ImageSize2 = 150px
| IUPACName = Glucose 1-phosphate | ImageCaption2 = Neutral form of α-<small>D</small>-glucose 1-phosphate
| IUPACName = <small>D</small>-Glucopyranosyl dihydrogen phosphate
⚫ | OtherNames =
| SystematicName = (2''Ξ'',3''R'',4''S'',5''S'',6''R'')-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl dihydrogen phosphate
⚫ | Section1 = {{Chembox Identifiers
⚫ | OtherNames = Cori ester
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 388311 | ChemSpiderID = 388311
| InChI = 1/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1 | InChI = 1/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1
Line 20: Line 22:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 59-56-3 | CASNo = 59-56-3
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 65533
| ChEBI = 16077 | UNII = CIX3U01VAU
⚫ | PubChem = 65533
| KEGG = C00103
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16077
| SMILES = O=P(O)(OC1O((O)(O)1O)CO)O | SMILES = O=P(O)(OC1O((O)(O)1O)CO)O
| MeSHName = glucose-1-phosphate | MeSHName = glucose-1-phosphate
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=6 | H=13 | O=9 | P=1
| Formula = C6H13O9P
| MolarMass = 260.136 | Appearance =
| Appearance = | Density =
| Density = | MeltingPt =
| MeltingPt = | BoilingPt =
| BoilingPt =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| Solubility = | MainHazards =
| MainHazards = | FlashPt =
| FlashPt = | AutoignitionPt =
| Autoignition =
}} }}
}} }}
⚫ '''Glucose 1-phosphate''' (also called '''cori ester''') is a ] molecule with a ] group on the 1'-carbon.


⚫ '''Glucose 1-phosphate''' (also called '''Cori ester''') is a ] molecule with a ] group on the 1'-carbon. It can exist in either the α- or β-]ic form.
==Reactions==

==Reactions of α-glucose 1-phosphate==
===Catabolic=== ===Catabolic===
In ], it is the direct product of the reaction in which ] cleaves off a ] of ] from a greater ] structure. In ], it is the direct product of the reaction in which ] cleaves off a ] of ] from a greater ] structure. A deficiency of muscle glycogen phosphorylase is known as ] (McArdle Disease).


To be utilized in cellular catabolism it must first be converted to ] by the ] ] in a free equilibrium.<ref>{{Citation|last=Pelley|first=John W.|title=8 - Gluconeogenesis and Glycogen Metabolism|date=2012-01-01|url=http://www.sciencedirect.com/science/article/pii/B9780323074469000088|work=Elsevier's Integrated Review Biochemistry (Second Edition)|pages=67–73|editor-last=Pelley|editor-first=John W.|place=Philadelphia|publisher=W.B. Saunders|language=en|doi=10.1016/b978-0-323-07446-9.00008-8|isbn=978-0-323-07446-9|access-date=2020-12-16}}</ref><ref>{{Citation|last=Isselbacher|first=Kurt J.|title=Galactose-1-phosphate Uridyl Transferase|date=1965-01-01|url=http://www.sciencedirect.com/science/article/pii/B9780123956309501535|work=Methods of Enzymatic Analysis|pages=863–866|editor-last=Bergmeyer|editor-first=Hans-Ulrich|publisher=Academic Press|language=en|doi=10.1016/b978-0-12-395630-9.50153-5|isbn=978-0-12-395630-9|access-date=2020-12-16}}</ref><ref>{{Citation|last=Bergmeyer|first=Hans-Ulrich|title=d-Glucose-1-phosphate|date=1965-01-01|url=http://www.sciencedirect.com/science/article/pii/B9780123956309500244|work=Methods of Enzymatic Analysis|pages=131–133|editor-last=Bergmeyer|editor-first=Hans-Ulrich|publisher=Academic Press|language=en|doi=10.1016/b978-0-12-395630-9.50024-4|isbn=978-0-12-395630-9|access-date=2020-12-16|last2=Klotzsch|first2=Helmut}}</ref> One reason that cells form glucose 1-phosphate instead of glucose during glycogen breakdown is that the very polar phosphorylated glucose cannot leave the cell membrane and so is marked for intracellular catabolism. ] deficiency is known as ] type 14 (GSD XIV).<ref></ref>
To be utilized in cellular catabolism it must first be converted to ] by the ] ]. One reason that cells form glucose 1-phosphate instead of glucose during glycogen breakdown is that the very polar phosphorylated glucose cannot leave the cell membrane and so is marked for intracellular catabolism.


===Anabolic=== ===Anabolic===
In ], free glucose 1-phosphate can also react with ] to form ], by using the enzyme ]. It can then return to the greater glycogen structure via ]. In ], free glucose 1-phosphate can also react with ] to form ],<ref name=":0">{{Citation|last=Blanco|first=Antonio|title=Chapter 19 - Integration and Regulation of Metabolism|date=2017-01-01|url=http://www.sciencedirect.com/science/article/pii/B9780128035504000197|work=Medical Biochemistry|pages=425–445|editor-last=Blanco|editor-first=Antonio|publisher=Academic Press|language=en|doi=10.1016/b978-0-12-803550-4.00019-7|isbn=978-0-12-803550-4|access-date=2020-12-16|last2=Blanco|first2=Gustavo|editor2-last=Blanco|editor2-first=Gustavo}}</ref> by using the enzyme ]. It can then return to the greater glycogen structure via ].<ref name=":0" />

==β-Glucose 1-phosphate==
β-Glucose 1-phosphate is found in some microbes. It is produced by inverting α-glucan phosphorylases including ], ] and ] and is then converted into ] by ].


==See also== ==See also==
* ] * ]
* ]


==References==
⚫ ]
{{reflist}}
⚫ ]


{{biochem-stub}}
{{Glycogenesis and glycogenolysis metabolic intermediates}} {{Glycogenesis and glycogenolysis metabolic intermediates}}
{{Fructose and galactose metabolic intermediates}} {{Fructose and galactose metabolic intermediates}}


⚫ ]
]
⚫ ]
]
]
]
]

Latest revision as of 01:26, 3 December 2023

Glucose 1-phosphate

Anionic form of α-D-glucose 1-phosphate

Neutral form of α-D-glucose 1-phosphate
Names
IUPAC name D-Glucopyranosyl dihydrogen phosphate
Systematic IUPAC name (2Ξ,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl dihydrogen phosphate
Other names Cori ester
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.396 Edit this at Wikidata
KEGG
MeSH glucose-1-phosphate
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1Key: HXXFSFRBOHSIMQ-GASJEMHNSA-N
  • InChI=1/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1Key: HXXFSFRBOHSIMQ-GASJEMHNBR
SMILES
  • O=P(O)(OC1O((O)(O)1O)CO)O
Properties
Chemical formula C6H13O9P
Molar mass 260.135 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Glucose 1-phosphate (also called Cori ester) is a glucose molecule with a phosphate group on the 1'-carbon. It can exist in either the α- or β-anomeric form.

Reactions of α-glucose 1-phosphate

Catabolic

In glycogenolysis, it is the direct product of the reaction in which glycogen phosphorylase cleaves off a molecule of glucose from a greater glycogen structure. A deficiency of muscle glycogen phosphorylase is known as glycogen storage disease type V (McArdle Disease).

To be utilized in cellular catabolism it must first be converted to glucose 6-phosphate by the enzyme phosphoglucomutase in a free equilibrium. One reason that cells form glucose 1-phosphate instead of glucose during glycogen breakdown is that the very polar phosphorylated glucose cannot leave the cell membrane and so is marked for intracellular catabolism. Phosphoglucomutase-1 deficiency is known as glycogen storage disease type 14 (GSD XIV).

Anabolic

In glycogenesis, free glucose 1-phosphate can also react with UTP to form UDP-glucose, by using the enzyme UDP-glucose pyrophosphorylase. It can then return to the greater glycogen structure via glycogen synthase.

β-Glucose 1-phosphate

β-Glucose 1-phosphate is found in some microbes. It is produced by inverting α-glucan phosphorylases including maltose phosphorylase, kojibiose phosphorylase and trehalose phosphorylase and is then converted into glucose 6-phosphate by β-phosphoglucomutase.

See also

References

  1. Pelley, John W. (2012-01-01), Pelley, John W. (ed.), "8 - Gluconeogenesis and Glycogen Metabolism", Elsevier's Integrated Review Biochemistry (Second Edition), Philadelphia: W.B. Saunders, pp. 67–73, doi:10.1016/b978-0-323-07446-9.00008-8, ISBN 978-0-323-07446-9, retrieved 2020-12-16
  2. Isselbacher, Kurt J. (1965-01-01), Bergmeyer, Hans-Ulrich (ed.), "Galactose-1-phosphate Uridyl Transferase", Methods of Enzymatic Analysis, Academic Press, pp. 863–866, doi:10.1016/b978-0-12-395630-9.50153-5, ISBN 978-0-12-395630-9, retrieved 2020-12-16
  3. Bergmeyer, Hans-Ulrich; Klotzsch, Helmut (1965-01-01), Bergmeyer, Hans-Ulrich (ed.), "d-Glucose-1-phosphate", Methods of Enzymatic Analysis, Academic Press, pp. 131–133, doi:10.1016/b978-0-12-395630-9.50024-4, ISBN 978-0-12-395630-9, retrieved 2020-12-16
  4. Orphanet: Glycogen storage disease due to phosphoglucomutase deficiency
  5. ^ Blanco, Antonio; Blanco, Gustavo (2017-01-01), Blanco, Antonio; Blanco, Gustavo (eds.), "Chapter 19 - Integration and Regulation of Metabolism", Medical Biochemistry, Academic Press, pp. 425–445, doi:10.1016/b978-0-12-803550-4.00019-7, ISBN 978-0-12-803550-4, retrieved 2020-12-16
Glycogenesis and glycogenolysis metabolic intermediates
Glucose
Uridine
Other
Fructose and galactose metabolic intermediates
Fructose
Galactose
Mannose
Categories: