glucose 1-phosphate
{{chembox
| Watchedfields = changed
| verifiedrevid = 443837963
| ImageFile = Glucose 1-phosphate.svg
| ImageSize = 150px
| ImageCaption = Anionic form of α-D-glucose 1-phosphate
| ImageFile2 =Cori_ester.png
| ImageSize2 = 150px
| ImageCaption2 = Neutral form of α-D-glucose 1-phosphate
| IUPACName = D-Glucopyranosyl dihydrogen phosphate
| SystematicName = (2Ξ,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl dihydrogen phosphate
| OtherNames = Cori ester
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| 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
| InChIKey = HXXFSFRBOHSIMQ-GASJEMHNBR
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HXXFSFRBOHSIMQ-GASJEMHNSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 59-56-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = CIX3U01VAU
| PubChem = 65533
| KEGG = C00103
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16077
| SMILES = O=P(O)(OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)O
| MeSHName = glucose-1-phosphate
}}
|Section2={{Chembox Properties
| C=6 | H=13 | O=9 | P=1
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|Section3={{Chembox Hazards
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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.{{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}}{{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}}{{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}} 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).[http://www.orpha.net/consor/cgi-bin/OC_Exp.php?Expert=711 Orphanet: Glycogen storage disease due to phosphoglucomutase deficiency]
=Anabolic=
In glycogenesis, free glucose 1-phosphate can also react with UTP to form UDP-glucose,{{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}} 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
{{reflist}}
{{Glycogenesis and glycogenolysis metabolic intermediates}}
{{Fructose and galactose metabolic intermediates}}