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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: α-D-glucose 1-phosphate

Synonyms: glucose 1-phosphate, cori ester, D-glucose 1-phosphate, glucose-1P, α-glucose-1-phosphate, D-glucose-α-1-phosphate, α-D-glucose-1-P, D-glucose-1-phosphate, α-D-glucopyranose 1-phosphate

Superclasses: all carbohydrates a carbohydrate a glycan a carbohydrate derivative a sugar phosphate a hexose phosphate a hexose 1-phosphate an alpha-hexose 1-phosphate
all carbohydrates a carbohydrate a glycan a carbohydrate derivative a sugar phosphate a hexose phosphate a hexose 1-phosphate D-glucose 1-phosphate
all carbohydrates a carbohydrate a glycan a carbohydrate derivative a sugar phosphate a sugar 1-phosphate a D-aldose 1-phosphate an alpha-D-aldose 1-phosphate
all carbohydrates a carbohydrate a glycan a carbohydrate derivative a sugar phosphate a sugar 1-phosphate a hexose 1-phosphate an alpha-hexose 1-phosphate
all carbohydrates a carbohydrate a glycan a carbohydrate derivative a sugar phosphate a sugar 1-phosphate a hexose 1-phosphate D-glucose 1-phosphate
all carbohydrates a carbohydrate a glycan a carbohydrate derivative an aldose phosphate an alpha-D-aldose 1-phosphate

Chemical Formula: C6H11O9P

Molecular Weight: 258.12 Daltons

Monoisotopic Molecular Weight: 260.0297185262 Daltons

SMILES: C(O)C1(OC(OP(=O)([O-])[O-])C(O)C(O)C(O)1)

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)/p-2/t2-,3-,4+,5-,6-/m1/s1

InChIKey: InChIKey=HXXFSFRBOHSIMQ-VFUOTHLCSA-L

Unification Links: CAS:59-56-3 , ChEBI:58601 , ChemSpider:5441206 , HMDB:HMDB01586 , IAF1260:33865 , KEGG:C00103 , MetaboLights:MTBLC58601 , PubChem:7091266

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -319.04593 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

D-galactose degradation V (Leloir pathway) , glycogenolysis II :
α-D-glucose 1-phosphate → D-glucopyranose 6-phosphate

extended VTC2 cycle :
GDP-β-L-galactose + α-D-glucose 1-phosphate → β-L-galactose 1-phosphate + GDP-α-D-glucose

GDP-glucose biosynthesis , GDP-glucose biosynthesis II :
α-D-glucose 1-phosphate + GTP + H+ → GDP-α-D-glucose + diphosphate

glucose and glucose-1-phosphate degradation :
α-D-glucose 1-phosphate + H2O → D-glucopyranose + phosphate

glycogen biosynthesis I (from ADP-D-Glucose) , starch biosynthesis :
α-D-glucose 1-phosphate + ATP + H+ → ADP-α-D-glucose + diphosphate

jadomycin biosynthesis :
α-D-glucose 1-phosphate + a nucleoside triphosphate + H+ → an NDP-α-D-glucose + diphosphate

Not in pathways:
a sugar phosphate + H2O → a sugar + phosphate

Reactions known to produce the compound:

glycogenolysis II :
a debranched limit dextrin + n phosphate → n α-D-glucose 1-phosphate

laminaribiose degradation :
laminaribiose + phosphate → β-D-glucose + α-D-glucose 1-phosphate

starch biosynthesis :
[(1→4)-α-D-glucosyl]n + phosphate → [(1→4)-α-D-glucosyl](n-1) + α-D-glucose 1-phosphate

sucrose biosynthesis II :
SHG-glucosyln+1 + phosphate → SHG-glucosyln + α-D-glucose 1-phosphate

sucrose degradation IV (sucrose phosphorylase) :
sucrose + phosphate → β-D-fructofuranose + α-D-glucose 1-phosphate

Not in pathways:
6-(D-glucose-1-phospho)-D-mannosylglycoprotein + H2O → α-D-glucose 1-phosphate + β-D-mannosyl-[glycoprotein] + H+


a UDP-sugar[periplasmic space] + H2O[periplasmic space] → UMP[periplasmic space] + an α-D-aldose 1-phosphate[periplasmic space] + 2 H+[periplasmic space]
an ADP-sugar + H2O → AMP + an α-D-aldose 1-phosphate


an N-acetyl-β-D-galactosalaminyl-[glycan] + H2O → a glycan + N-acetyl-β-D-galactosamine

Reactions known to both consume and produce the compound:

CDP-4-dehydro-3,6-dideoxy-D-glucose biosynthesis :
α-D-glucose 1-phosphate + CTP + H+ ↔ CDP-α-D-glucose + diphosphate

chitin biosynthesis :
α-D-glucose 1-phosphate + UTP + H+ ↔ UDP-α-D-glucose + diphosphate

D-galactose degradation V (Leloir pathway) :
UDP-α-D-glucose + α-D-galactose 1-phosphate ↔ UDP-α-D-galactose + α-D-glucose 1-phosphate

dTDP-3-acetamido-3,6-dideoxy-α-D-galactose biosynthesis , dTDP-3-acetamido-3,6-dideoxy-α-D-glucose biosynthesis , dTDP-6-deoxy-α-D-allose biosynthesis , dTDP-α-D-mycaminose biosynthesis , dTDP-β-L-4-epi-vancosamine biosynthesis , dTDP-β-L-noviose biosynthesis , dTDP-D-β-fucofuranose biosynthesis , dTDP-D-desosamine biosynthesis , dTDP-D-forosamine biosynthesis , dTDP-D-olivose, dTDP-D-oliose and dTDP-D-mycarose biosynthesis , dTDP-L-megosamine biosynthesis , dTDP-L-mycarose biosynthesis , dTDP-L-olivose biosynthesis , dTDP-L-rhamnose biosynthesis I , dTDP-L-rhamnose biosynthesis II , dTDP-N-acetylthomosamine biosynthesis , dTDP-N-acetylviosamine biosynthesis :
α-D-glucose 1-phosphate + dTTP + H+ ↔ dTDP-α-D-glucose + diphosphate

galactose degradation I (Leloir pathway) :
UDP-α-D-glucose + α-D-galactose 1-phosphate ↔ UDP-α-D-galactose + α-D-glucose 1-phosphate
α-D-glucose 1-phosphate ↔ β-D-glucose 1-phosphate

GDP-glucose biosynthesis , GDP-glucose biosynthesis II , glucose and glucose-1-phosphate degradation , glycogen biosynthesis I (from ADP-D-Glucose) , starch biosynthesis , sucrose degradation IV (sucrose phosphorylase) :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate

glycogen degradation I :
a glycogen + phosphate ↔ a limit dextrin + α-D-glucose 1-phosphate
maltotetraose + phosphate ↔ maltotriose + α-D-glucose 1-phosphate
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate

glycogenolysis II :
a glycogen + phosphate ↔ a limit dextrin + α-D-glucose 1-phosphate

stachyose degradation :
UDP-α-D-glucose + α-D-galactose 1-phosphate ↔ UDP-α-D-galactose + α-D-glucose 1-phosphate
α-D-glucose 1-phosphate + UTP + H+ ↔ UDP-α-D-glucose + diphosphate

starch degradation III :
a maltodextrin(n) + phosphate ↔ a maltodextrin(n-1) + α-D-glucose 1-phosphate
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate

starch degradation V :
a maltodextrin(n) + phosphate ↔ a maltodextrin(n-1) + α-D-glucose 1-phosphate
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate

streptomycin biosynthesis :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 1-phosphate + CTP + H+ ↔ CDP-α-D-glucose + diphosphate

sucrose biosynthesis II :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 1-phosphate + UTP + H+ ↔ UDP-α-D-glucose + diphosphate

sucrose degradation II (sucrose synthase) :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 1-phosphate + UTP + H+ ↔ UDP-α-D-glucose + diphosphate

trehalose degradation V :
α,α-trehalose + phosphate ↔ α-D-glucose + α-D-glucose 1-phosphate
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate

UDP-glucose biosynthesis :
α-D-glucose 1-phosphate ↔ α-D-glucose 6-phosphate
α-D-glucose 1-phosphate + UTP + H+ ↔ UDP-α-D-glucose + diphosphate

Not in pathways:
(1,4-α-D-glucosyl)(n) + phosphate ↔ (1,4-α-D-glucosyl)(n-1) + α-D-glucose 1-phosphate
GDP-α-D-glucose + phosphate ↔ α-D-glucose 1-phosphate + GDP + H+
cellobionate + phosphate ↔ α-D-glucose 1-phosphate + D-gluconate
sucrose 6F-phosphate + phosphate ↔ α-D-glucose 1-phosphate + β-D-fructofuranose 6-phosphate

In Reactions of unknown directionality:

Not in pathways:
ADP-α-D-glucose + H2O = AMP + α-D-glucose 1-phosphate + 2 H+
a linear malto-oligosaccharide [(glucose)n] + phosphate = α-D-glucose 1-phosphate + a linear malto-oligosaccharide [(glucose)n-1]
a glycogen + phosphate = α-D-glucose 1-phosphate + maltotetraose
a cellodextrin + phosphate = (1,4-β-D-glucosyl)(n-1) + α-D-glucose 1-phosphate
1,3-β-D-glucan(n) + phosphate = α-D-glucose 1-phosphate + 1,3-β-D-glucan(n-1)
maltopentaose + phosphate = α-D-glucose 1-phosphate + maltotetraose
maltohexaose + phosphate = maltopentaose + α-D-glucose 1-phosphate
maltoheptaose + phosphate = maltohexaose + α-D-glucose 1-phosphate
β-D-cellobiose + phosphate = α-D-glucose 1-phosphate + β-D-glucose
(1→6)-β-D-glucosyl-[(1→3)-β-D-glucosyl]n + phosphate = α-D-glucose 1-phosphate + (1→6)-β-D-glucosyl-[(1→3)-β-D-glucosyl]n-1
(1,2-β-D-glucosyl)(n) + phosphate = (1,2-β-D-glucosyl)(n-1) + α-D-glucose 1-phosphate
2 α-D-glucose 1-phosphate + H2O = maltose + 2 phosphate
2 α-D-glucose 1-phosphate = α-glucose 1,6-bisphosphate + β-D-glucose
α-D-glucose 1-phosphate + 1,3-bisphospho-D-glycerate = α-glucose 1,6-bisphosphate + 3-phospho-D-glycerate + H+
α-D-glucose 1-phosphate + ATP = α-glucose 1,6-bisphosphate + ADP + H+
riboflavin + α-D-glucose 1-phosphate = β-D-glucose + FMN


a nucleoside triphosphate + an α-D-aldose 1-phosphate + H+ = a nucleoside diphosphate-hexose + diphosphate
an α-D-aldose 1-phosphate + ADP + H+ = an ADP-aldose + phosphate
an α-D-aldose 1-phosphate + a nucleoside diphosphate + H+ = a nucleotide diphosphate-aldose + phosphate


phosphoramidate + a D-hexose = an α-hexose 1-phosphate + ammonium


UTP + a sugar 1-phosphate = a UDP-sugar + diphosphate

In Transport reactions:
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[out] → a [PTS enzyme I]-L-histidine + a sugar phosphate[in]

Enzymes activated by α-D-glucose 1-phosphate, sorted by the type of activation, are:

Activator (Allosteric) of: NAD+-dependent glyceraldehyde-3-phosphate dehydrogenase [Brunner98]

Enzymes inhibited by α-D-glucose 1-phosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: phosphoglucomutase [Comment 1]

Inhibitor (Mechanism unknown) of: triose phosphate isomerase [Tomlinson79]


References

Brunner98: Brunner NA, Brinkmann H, Siebers B, Hensel R (1998). "NAD+-dependent glyceraldehyde-3-phosphate dehydrogenase from Thermoproteus tenax. The first identified archaeal member of the aldehyde dehydrogenase superfamily is a glycolytic enzyme with unusual regulatory properties." J Biol Chem 273(11);6149-56. PMID: 9497334

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Ray64: Ray WJ Jr., Roscelli GA (1964). "A kinetic study of the phosphoglucomutase pathway." J Biol Chem 239:1228-1236.

Tomlinson79: Tomlinson J.D., Turner J.F. "Pea seed triose phosphate isomerase." Phytochemistry (1979) 18:1959-1962.


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Wed Nov 26, 2014, biocyc13.