Glucose 1-phosphate

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	59-56-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16077 ;
ChemSpider	388311 ;
ECHA InfoCard	100.000.396
KEGG	C00103;
MeSH	glucose-1-phosphate
PubChem CID	65533;
UNII	CIX3U01VAU ;
CompTox Dashboard (EPA)	DTXSID90889321 ;
	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/s1 Key: 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/s1 Key: HXXFSFRBOHSIMQ-GASJEMHNBR;
	SMILES O=P(O)(OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)O;
Properties
Chemical formula	C6H13O9P
Molar mass	260.135 g·mol−1
	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

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.^[1]^[2]^[3] 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).^[4]

Anabolic

In glycogenesis, free glucose 1-phosphate can also react with UTP to form UDP-glucose,^[5] by using the enzyme UDP-glucose pyrophosphorylase. It can then return to the greater glycogen structure via glycogen synthase.^[5]

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.

References

^ 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
^ 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
^ 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
^ Orphanet: Glycogen storage disease due to phosphoglucomutase deficiency
^ ^a ^b 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

[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

[:0-5] 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

[1]

[2]

[3]

[4]

[5]

v t e Glycogenesis and glycogenolysis metabolic intermediates
Glucose	Glucose 6-phosphate Glucose 1-phosphate
Uridine	Uridine diphosphate glucose Uridine triphosphate
Other	Glycogen Limit dextran

Names
Anionic form of α-D-glucose 1-phosphate
Neutral form of α-D-glucose 1-phosphate
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	59-56-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16077^Y
ChemSpider	388311^Y
ECHA InfoCard	100.000.396
KEGG	C00103
MeSH	glucose-1-phosphate
PubChem CID	65533
UNII	CIX3U01VAU^Y
CompTox Dashboard (EPA)	DTXSID90889321
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/s1^Y Key: HXXFSFRBOHSIMQ-GASJEMHNSA-N^Y 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 Key: HXXFSFRBOHSIMQ-GASJEMHNBR
SMILES O=P(O)(OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)O
Properties
Chemical formula	C₆H₁₃O₉P
Molar mass	260.135 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references