Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB000423
Identification
Name: Glucose 1-phosphate
Description:Glucose 1-phosphate is the direct product of the reaction in which glycogen phosphorylase cleaves off a molecule of glucose from a greater glycogen structure. Glycogen phosphorylase, the product of the glgP Gene, catalyzes glycogen breakdown by removing glucose units from the nonreducing ends in Pseudomonas aeruginosa. It cannot travel down many metabolic pathways and must be interconverted by the enzyme phosphoglucomutase in order to become glucose 6-phosphate. In glycogenesis, free glucose 1-phosphate can also react with UTP to form UDP-glucose, by using the enzyme UDP-glucose pyrophosphorylase. Periplasmic acid glucose-1-phosphatase (G-1-Pase) encoded by gene Agp is necessary for the growth of Pseudomonas aeruginosa in a minimal medium containing glucose-1-phosphate (G-1-P) as the sole source of carbon.
Structure
Thumb
Synonyms:
  • α-D-glucose-1-P
  • α-glucose-1-phosphate
  • α-glucose-1-phosphoric acid
  • A-D-Glucopyranosyl phosphate
  • a-D-Glucopyranosyl phosphoric acid
  • A-D-Glucose 1-phosphate
  • a-D-Glucose 1-phosphoric acid
  • a-D-Glucose-1-P
  • A-D-Glucose-1-phosphate
  • a-D-Glucose-1-phosphoric acid
  • a-delta-Glucopyranosyl phosphate
  • a-delta-Glucopyranosyl phosphoric acid
  • a-delta-Glucose 1-phosphate
  • a-delta-Glucose 1-phosphoric acid
  • a-delta-Glucose-1-phosphate
  • a-delta-Glucose-1-phosphoric acid
  • a-Glucose-1-phosphate
  • a-Glucose-1-phosphoric acid
  • a-δ-Glucopyranosyl phosphate
  • a-δ-Glucopyranosyl phosphoric acid
  • a-δ-Glucose 1-phosphate
  • a-δ-Glucose 1-phosphoric acid
  • a-δ-Glucose-1-phosphate
  • a-δ-Glucose-1-phosphoric acid
  • Alpha-D-Glucopyranosyl phosphate
  • alpha-D-Glucopyranosyl phosphoric acid
  • Alpha-D-Glucose 1-phosphate
  • alpha-D-Glucose 1-phosphoric acid
  • Alpha-D-Glucose-1-P
  • Alpha-D-Glucose-1-phosphate
  • alpha-D-Glucose-1-phosphoric acid
  • Alpha-delta-Glucopyranosyl phosphate
  • alpha-delta-Glucopyranosyl phosphoric acid
  • Alpha-delta-Glucose 1-phosphate
  • alpha-delta-Glucose 1-phosphoric acid
  • Alpha-delta-glucose-1-phosphate
  • alpha-delta-Glucose-1-phosphoric acid
  • Alpha-Glucose-1-phosphate
  • alpha-Glucose-1-phosphoric acid
  • Cori ester
  • D-Glucopyranose 1-phosphate
  • D-Glucopyranose 1-phosphoric acid
  • D-Glucose 1-phosphate
  • D-Glucose 1-phosphoric acid
  • D-glucose-α-1-phosphate
  • D-Glucose-α-1-phosphoric acid
  • D-Glucose-1-P
  • D-Glucose-1-phosphate
  • D-Glucose-1-phosphoric acid
  • D-Glucose-a-1-phosphate
  • D-Glucose-a-1-phosphoric acid
  • D-Glucose-alpha-1-phosphate
  • D-Glucose-alpha-1-phosphoric acid
  • D-Glucose-α-1-phosphate
  • D-Glucose-α-1-phosphoric acid
  • Delta-Glucopyranose 1-phosphate
  • delta-Glucopyranose 1-phosphoric acid
  • Delta-Glucose 1-phosphate
  • delta-Glucose 1-phosphoric acid
  • Delta-Glucose-1-P
  • Delta-Glucose-1-phosphate
  • delta-Glucose-1-phosphoric acid
  • Glucose 1-phosphate
  • Glucose 1-phosphoric acid
  • Glucose monophosphate
  • Glucose monophosphoric acid
  • Glucose-1-phosphate
  • Glucose-1-phosphoric acid
  • Glucose-1P
  • α-D-Glucopyranosyl phosphate
  • α-D-Glucopyranosyl phosphoric acid
  • α-D-Glucose 1-phosphate
  • α-D-Glucose 1-phosphoric acid
  • α-D-Glucose-1-P
  • α-D-Glucose-1-phosphate
  • α-D-Glucose-1-phosphoric acid
  • α-Glucose-1-phosphate
  • α-Glucose-1-phosphoric acid
  • α-δ-Glucopyranosyl phosphate
  • α-δ-Glucopyranosyl phosphoric acid
  • α-δ-Glucose 1-phosphate
  • α-δ-Glucose 1-phosphoric acid
  • α-δ-Glucose-1-phosphate
  • α-δ-Glucose-1-phosphoric acid
  • δ-Glucopyranose 1-phosphate
  • δ-Glucopyranose 1-phosphoric acid
  • δ-Glucose 1-phosphate
  • δ-Glucose 1-phosphoric acid
  • δ-Glucose-1-P
  • δ-Glucose-1-phosphate
  • δ-Glucose-1-phosphoric acid
Chemical Formula: C6H13O9P
Average Molecular Weight: 260.1358
Monoisotopic Molecular Weight: 260.029718526
InChI Key: HXXFSFRBOHSIMQ-VFUOTHLCSA-N
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
CAS number: 59-56-3
IUPAC Name:{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name: α-D-glucose 1-phosphate
SMILES:OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct Parent Monosaccharide phosphates
Alternative Parents
Substituents
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Water Solubility:1000.0 mg/mL [MERCK INDEX (1996)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility32.3 mg/mLALOGPS
logP-2ALOGPS
logP-3.1ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m3·mol-1ChemAxon
Polarizability20.72 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
References:
  • Arthur PG, Kent JC, Hartmann PE: Microanalysis of the metabolic intermediates of lactose synthesis in human milk and plasma using bioluminescent methods. Anal Biochem. 1989 Feb 1;176(2):449-56. Pubmed: 2742136
  • Bollaert PE, Levy B, Nace L, Laterre PF, Larcan A: Hemodynamic and metabolic effects of rapid correction of hypophosphatemia in patients with septic shock. Chest. 1995 Jun;107(6):1698-701. Pubmed: 7781370
  • Chen YT, Kato T: Liver-specific glucose-6-phosphatase is not present in human placenta. J Inherit Metab Dis. 1985;8(2):92-4. Pubmed: 3023746
  • Gannon MC, Khan MA, Nuttall FQ: Glucose appearance rate after the ingestion of galactose. Metabolism. 2001 Jan;50(1):93-8. Pubmed: 11172481
  • Gella FJ, Cusso R: Glycogen phosphorylase from normal and leukemic human leucocytes: kinetic parameters of the active form. Rev Esp Fisiol. 1980 Mar;36(1):1-6. Pubmed: 7394270
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Kamei A, Kato M: Contribution of glycation to human lens coloration. Chem Pharm Bull (Tokyo). 1991 May;39(5):1272-6. Pubmed: 1914002
  • Kamei A: Glycation and insolubility of human lens protein. Chem Pharm Bull (Tokyo). 1992 Oct;40(10):2787-91. Pubmed: 1464110
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kodentsova VM, Glinka EIu: [Changes in kinetic properties of pyridoxal-dependent enzymes during dietary vitamin B6 deficiency in rats] Ukr Biokhim Zh. 1990 Jan-Feb;62(1):44-9. Pubmed: 2110692
  • Krause EG, Will H, Bohm M, Wollenberger A: The assay of glycogen phosphorylase in human blood serum and its application to the diagnosis of myocardial infarction. Clin Chim Acta. 1975 Jan 20;58(2):145-54. Pubmed: 1122638
  • Lai K, Elsas LJ: Structure-function analyses of a common mutation in blacks with transferase-deficiency galactosemia. Mol Genet Metab. 2001 Sep-Oct;74(1-2):264-72. Pubmed: 11592823
  • Lang A, Groebe H, Hellkuhl B, von Figura K: A new variant of galactosemia: galactose-1-phosphate uridylytransferase sensitive to product inhibition by glucose 1-phosphate. Pediatr Res. 1980 May;14(5):729-34. Pubmed: 6247691
  • Lederer B, Van Hoof F, Van den Berghe G, Hers H: Glycogen phosphorylase and its converter enzymes in haemolysates of normal human subjects and of patients with type VI glycogen-storage disease. A study of phosphorylase kinase deficiency. Biochem J. 1975 Apr;147(1):23-35. Pubmed: 168880
  • Leuzzi R, Fulceri R, Marcolongo P, Banhegyi G, Zammarchi E, Stafford K, Burchell A, Benedetti A: Glucose 6-phosphate transport in fibroblast microsomes from glycogen storage disease type 1b patients: evidence for multiple glucose 6-phosphate transport systems. Biochem J. 2001 Jul 15;357(Pt 2):557-62. Pubmed: 11439108
  • Mahadevan-Jansen A, Mitchell MF, Ramanujam N, Malpica A, Thomsen S, Utzinger U, Richards-Kortum R: Near-infrared Raman spectroscopy for in vitro detection of cervical precancers. Photochem Photobiol. 1998 Jul;68(1):123-32. Pubmed: 9679458
  • Nakashima H, Suo H, Ochiai J, Sugie H, Kawamura Y: [A case of adult onset phosphoglucomutase deficiency] Rinsho Shinkeigaku. 1992 Jan;32(1):42-7. Pubmed: 1385770
  • Palombi M, Bochicchio O, Gargiulo M, Sammarco M: [Alternative therapy of deep venous thrombosis in patients at hemorrhagic risk] Minerva Chir. 1994 Mar;49(3):189-94. Pubmed: 8028729
  • Park, C., Park, C., Lee, Y., Lee, S.Y., Oh, H.B., Lee, J. (2011) Determination of the Intracellular Concentration of Metabolites in Escherichia coli Collected during the Exponential and Stationary Growth Phases using Liquid Chromatography-Mass Spectrometry. Bull Korean Chem. Soc. 32: 524-530.
  • Pezzarossa A, Cavazzini G, Coscelli C, Butturini U: [Modifications induced by glucose-1-phosphate on carbohydrate utilization curve after venous loading. Results in normal subjects (preliminary note)] Boll Soc Ital Biol Sper. 1972 Jun 30;48(12):318-21. Pubmed: 5070100
  • Reinken L, Obladen M, Dockx-Reinken F, Lindemann C: [The effect of osteopenia prevention in very small premature infants on hormonal parameters of calcium metabolism and bone mineralization] Klin Padiatr. 1989 May-Jun;201(3):177-82. Pubmed: 2739343
  • Suzuki K, Kayamori Y, Katayama Y: Development of an enzymatic method for the assay of serum magnesium using phosphoglucomutase and glucose-6-phosphate dehydrogenase. Clin Biochem. 1991 Jun;24(3):249-53. Pubmed: 1831412
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yamada Y, Kono N, Nakajima H, Shimizu T, Kiyokawa H, Kawachi M, Ono A, Nishimura T, Kuwajima M, Tarui S: Low glucose-1, 6-bisphosphate and high fructose-2, 6-bisphosphate concentrations in muscles of patients with glycogenosis types VII and V. Biochem Biophys Res Commun. 1991 Apr 15;176(1):7-10. Pubmed: 2018547
Synthesis Reference: Weinhausel, Andreas; Nidetzky, Bernd; Kysela, Christian; Kulbe, Klaus D. Application of Escherichia coli maltodextrin-phosphorylase for the continuous production of glucose-1-phosphate. Enzyme and Microbial Technology (1995), 17(2), 140-6.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID29042
HMDB IDHMDB01586
Pubchem Compound ID65533
Kegg IDC00103
ChemSpider ID388311
WikipediaGlucose 1-phosphate
BioCyc IDGLC-1-P
EcoCyc IDGLC-1-P

Enzymes

General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties
Gene Name:
glgP
Locus Tag:
PA2144
Molecular weight:
92 kDa
Reactions
(1,4-alpha-D-glucosyl)(n) + phosphate = (1,4-alpha-D-glucosyl)(n-1) + alpha-D-glucose 1-phosphate.
General function:
Involved in UTP:glucose-1-phosphate uridylyltransferase activity
Specific function:
May play a role in stationary phase survival
Gene Name:
galU
Locus Tag:
PA2023
Molecular weight:
31.2 kDa
Reactions
UTP + alpha-D-glucose 1-phosphate = diphosphate + UDP-glucose.
General function:
Involved in nucleoside-triphosphate diphosphatase activity
Specific function:
Specific function unknown
Gene Name:
mazG
Locus Tag:
PA0935
Molecular weight:
31.2 kDa
Reactions
ATP + H(2)O = AMP + diphosphate.
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose
Gene Name:
pgm
Locus Tag:
PA5131
Molecular weight:
55.6 kDa
Reactions
Alpha-D-glucose 1-phosphate = alpha-D-glucose 6-phosphate.
General function:
Involved in glucose-1-phosphate thymidylyltransferase activity
Specific function:
Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis
Gene Name:
rmlA1
Locus Tag:
PA5163
Molecular weight:
32.5 kDa
Reactions
dTTP + alpha-D-glucose 1-phosphate = diphosphate + dTDP-glucose.

Transporters