Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-06-29 00:47:02 UTC |
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NP-MRD ID | NP0001389 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Glucose 6-phosphate |
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Description | Glucose 6-phosphate (G6P, sometimes called the Robison ester) is a glucose sugar phosphorylated at the hydroxy group on carbon 6. Glucose 6-phosphate (G6P) has two anomers: The alpha anomer and the beta anomer. Glucose 6-phosphate is an ester of glucose with phosphoric acid, made in the course of glucose metabolism by mammalian and other cells. It is a normal constituent of resting muscle and probably is in constant equilibrium with fructose 6-phosphate (Stedman, 26th ed). When glucose enters a cell, it is immediately phosphorylated to G6P. This is catalyzed with hexokinase enzymes, thus consuming one ATP. A major reason for immediate phosphorylation of the glucose is so that it cannot diffuse out of the cell. The phosphorylation adds a charged group so the G6P cannot easily cross cell membranes. G6P can travel down two metabolic pathways: Glycolysis and the pentose phosphate pathway. In addition to the metabolic pathways, G6P can also be stored as glycogen in the liver if blood glucose levels are high. If the body needs energy or carbon skeletons for syntheses, G6P can be isomerized to fructose 6-phosphate and then phosphorylated to fructose 1,6-bisphosphate. Note, the molecule now has 2 phosphoryl groups attached. The addition of the 2nd phosphoryl group is an irreversible step, so once this happens G6P will enter glycolysis and be turned into pyruvate (ATP production occurs). If blood glucose levels are high, the body needs a way to store the excess glucose. After being converted to G6P, phosphoglucose mutase (an isomerase) can turn the molecule into glucose 1-phosphate. Glucose 1-phosphate can then be combined with uridine triphosphate (UTP) to form UDP-glucose. This reaction is driven by the hydrolysis of pyrophosphate that is released in the reaction. Now, the activated UDP-glucose can add to a growing glycogen molecule with the help of glycogen synthase. This is a very efficient storage mechanism for glucose since it costs the body only 1 ATP to store the 1 glucose molecule and virtually no energy to remove it from storage. It is important to note that glucose 6-phosphate is an allosteric activator of glycogen synthase, which makes sense because when the level of glucose is high the body should store the excess glucose as glycogen. On the other hand, glycogen synthase is inhibited when it is phosphorylated by protein kinase during times of high stress or low blood glucose levels. |
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Structure | OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1 |
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Synonyms | Value | Source |
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6-O-Phosphono-D-glucopyranose | ChEBI | D-Glucose 6-phosphate | ChEBI | GLC6p | ChEBI | Robison ester | ChEBI | D-Glucose 6-phosphoric acid | Generator | Glucose 6-phosphoric acid | Generator | a-D-Glucose 6- phosphate | HMDB | alpha-D-Glucose 6- phosphate | HMDB | alpha-D-Glucose 6-phosphate | HMDB | alpha-D-Hexose 6-phosphate | HMDB | D(+)-Glucopyranose 6-phosphate | HMDB | D-Glucose-6-dihydrogen phosphate | HMDB | D-Hexose 6-phosphate | HMDB | Glucose-6-phosphate | HMDB | D-Glucopyranose 6-phosphoric acid | HMDB | Glucose 6-phosphate | KEGG |
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Chemical Formula | C6H13O9P |
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Average Mass | 260.1358 Da |
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Monoisotopic Mass | 260.02972 Da |
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IUPAC Name | {[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid |
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Traditional Name | glucose 6-phosphate |
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CAS Registry Number | 56-73-5 |
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SMILES | OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1 |
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InChI Key | NBSCHQHZLSJFNQ-GASJEMHNSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Hexose phosphates |
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Alternative Parents | |
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Substituents | - Hexose phosphate
- Monosaccharide phosphate
- Monoalkyl phosphate
- Organic phosphoric acid derivative
- Alkyl phosphate
- Oxane
- Phosphoric acid ester
- Hemiacetal
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Liquid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. [PubMed:15882454 ]
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- Roden M: How free fatty acids inhibit glucose utilization in human skeletal muscle. News Physiol Sci. 2004 Jun;19:92-6. [PubMed:15143200 ]
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- Schalin-Jantti C, Harkonen M, Groop LC: Impaired activation of glycogen synthase in people at increased risk for developing NIDDM. Diabetes. 1992 May;41(5):598-604. [PubMed:1568529 ]
- Vaag A, Damsbo P, Hother-Nielsen O, Beck-Nielsen H: Hyperglycaemia compensates for the defects in insulin-mediated glucose metabolism and in the activation of glycogen synthase in the skeletal muscle of patients with type 2 (non-insulin-dependent) diabetes mellitus. Diabetologia. 1992 Jan;35(1):80-8. [PubMed:1541385 ]
- Fortpied J, Maliekal P, Vertommen D, Van Schaftingen E: Magnesium-dependent phosphatase-1 is a protein-fructosamine-6-phosphatase potentially involved in glycation repair. J Biol Chem. 2006 Jul 7;281(27):18378-85. Epub 2006 May 1. [PubMed:16670083 ]
- Cline GW, Petersen KF, Krssak M, Shen J, Hundal RS, Trajanoski Z, Inzucchi S, Dresner A, Rothman DL, Shulman GI: Impaired glucose transport as a cause of decreased insulin-stimulated muscle glycogen synthesis in type 2 diabetes. N Engl J Med. 1999 Jul 22;341(4):240-6. [PubMed:10413736 ]
- Turvey EA, Heigenhauser GJ, Parolin M, Peters SJ: Elevated n-3 fatty acids in a high-fat diet attenuate the increase in PDH kinase activity but not PDH activity in human skeletal muscle. J Appl Physiol (1985). 2005 Jan;98(1):350-5. [PubMed:15591305 ]
- Benkoel L, Chamlian A, Barrat E, Laffargue P: The use of ferricyanide for the electron microscopic demonstration of dehydrogenases in human steroidogenic cells. J Histochem Cytochem. 1976 Nov;24(11):1194-203. [PubMed:1002973 ]
- Villar-Palasi C, Guinovart JJ: The role of glucose 6-phosphate in the control of glycogen synthase. FASEB J. 1997 Jun;11(7):544-58. [PubMed:9212078 ]
- Vestergaard H, Bjorbaek C, Hansen T, Larsen FS, Granner DK, Pedersen O: Impaired activity and gene expression of hexokinase II in muscle from non-insulin-dependent diabetes mellitus patients. J Clin Invest. 1995 Dec;96(6):2639-45. [PubMed:8675629 ]
- Roussel R, Carlier PG, Wary C, Velho G, Bloch G: Evidence for 100% 13C NMR visibility of glucose in human skeletal muscle. Magn Reson Med. 1997 Jun;37(6):821-4. [PubMed:9178231 ]
- Petersen KF, Hendler R, Price T, Perseghin G, Rothman DL, Held N, Amatruda JM, Shulman GI: 13C/31P NMR studies on the mechanism of insulin resistance in obesity. Diabetes. 1998 Mar;47(3):381-6. [PubMed:9519743 ]
- Boden G, Chen X, Ruiz J, White JV, Rossetti L: Mechanisms of fatty acid-induced inhibition of glucose uptake. J Clin Invest. 1994 Jun;93(6):2438-46. [PubMed:8200979 ]
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