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MetaCyc Compound: α-D-glucopyranose 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-glucose 1-phosphate

Superclasses: all carbohydratesa carbohydratea glycana carbohydrate derivativea sugar phosphatea hexose phosphatea hexose 1-phosphatean alpha-hexose 1-phosphate
all carbohydratesa carbohydratea glycana carbohydrate derivativea sugar phosphatea hexose phosphatea hexose 1-phosphateD-glucose 1-phosphate
all carbohydratesa carbohydratea glycana carbohydrate derivativea sugar phosphatea sugar 1-phosphatea D-aldose 1-phosphatean alpha-D-aldose 1-phosphate
all carbohydratesa carbohydratea glycana carbohydrate derivativea sugar phosphatea sugar 1-phosphatea hexose 1-phosphatean alpha-hexose 1-phosphate
all carbohydratesa carbohydratea glycana carbohydrate derivativea sugar phosphatea sugar 1-phosphatea hexose 1-phosphateD-glucose 1-phosphate
all carbohydratesa carbohydratea glycana carbohydrate derivativean aldose phosphatean alpha-D-aldose 1-phosphate

Chemical Formula: C6H11O9P

Molecular Weight: 258.12 Daltons

Monoisotopic Molecular Weight: 260.0297185262 Daltons

α-D-glucopyranose 1-phosphate compound structure

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 Formation (ΔfG in kcal/mol): -319.04593Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

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

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

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

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

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

Reactions known to produce the compound:

glycogen degradation I , glycogen degradation II :
a debranched α-limit dextrin + n phosphate → n α-D-glucopyranose 1-phosphate

laminaribiose degradation :
laminaribiose + phosphate → D-glucopyranose + α-D-glucopyranose 1-phosphate

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

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

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

Not in pathways:
a UDP-sugar[periplasm] + H2O[periplasm] → UMP[periplasm] + an α-D-aldose 1-phosphate[periplasm] + 2 H+[periplasm]
an ADP-sugar + H2O → AMP + an α-D-aldose 1-phosphate

Reactions known to both consume and produce the compound:

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

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

D-galactose degradation V (Leloir pathway) :
UDP-α-D-glucose + α-D-galactose 1-phosphate ↔ UDP-α-D-galactose + α-D-glucopyranose 1-phosphate
α-D-glucopyranose 1-phosphate ↔ D-glucopyranose 6-phosphate

dTDP-3-acetamido-3,6-dideoxy-α-D-glucose biosynthesis , dTDP-3-acetamido-α-D-fucos biosynthesis , dTDP-4-O-demethyl-β-L-noviose biosynthesis , dTDP-6-deoxy-α-D-allose biosynthesis , dTDP-α-D-mycaminose biosynthesis , dTDP-β-L-4-epi-vancosamine biosynthesis , dTDP-β-L-digitoxose 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-D-ravidosamine and dTDP-4-acetyl-D-ravidosamine 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-glucopyranose 1-phosphate + dTTP + H+ ↔ dTDP-α-D-glucose + diphosphate

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

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

glycogen degradation II :
a glycogen + phosphate ↔ an α-limit dextrin + α-D-glucopyranose 1-phosphate
α-D-glucopyranose 1-phosphate ↔ D-glucopyranose 6-phosphate

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

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

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

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

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

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

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

In Reactions of unknown directionality:

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

Not in pathways:
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

Not in pathways:
phosphoramidate + a D-hexose = an α-hexose 1-phosphate + ammonium

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-glucopyranose 1-phosphate, sorted by the type of activation, are:

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

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

Inhibitor (Competitive) of: phosphoglucomutase [Comment 1] Inhibitor (Mechanism unknown) of: triose phosphate isomerase [Tomlinson79]

This compound has been characterized as an alternative substrate of the following enzymes: sucrose 3-dehydrogenase, 3-phytase, UDP-sugar pyrophosphorylase, UDP-N-acetylglucosamine pyrophosphorylase, octose 1-phosphate guanylyltransferase, sucrose phosphorylase, glucosamine-1-phosphate guanylyltransferase, inositol monopohsphatase, phosphoglucosamine mutase, sugar phosphatase


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."

Ray64a: 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.


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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