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α-D-Glucose-1-phosphate

Cat No.:V107109 Purity: ≥98%
α-D-Glucose-1-phosphate is an important intermediate in sugar metabolism. It can act as a glycosyl donor in glycoside transfer reactions and participate in the synthesis and decomposition of glycogen through the action of phosphorylase.
α-D-Glucose-1-phosphate
α-D-Glucose-1-phosphate Chemical Structure CAS No.: 59-56-3
Product category: Biochemical Assay Reagents
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
Other Sizes

Other Forms of α-D-Glucose-1-phosphate:

  • α-D-Glucose-1-phosphate disodium
  • α-D-Glucopyranose,1-dihydrogen phosphate (potassium)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
α-D-Glucose-1-phosphate is an important intermediate in sugar metabolism. It can serve as a glycosyl donor in glycoside transfer reactions and participate in the synthesis and decomposition of glycogen through the action of phosphorylase.
alpha-D-Glucose-1-phosphate (CAS: 59-56-3) is a pivotal biochemical reagent and a naturally occurring intermediate in carbohydrate metabolism. It is the product of glycogen breakdown by the enzyme glycogen phosphorylase and serves as the primary building block for the synthesis of glycogen. In plants, it is the immediate precursor to starch. This compound functions as a glycosyl donor in glycosyl transfer reactions and is essential for the study of metabolic enzymes such as phosphorylases. It is a conjugate acid of a D-glucopyranose 1-phosphate(2-).
Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite
The biological targets of alpha-D-Glucose-1-phosphate are a series of metabolic enzymes that use it as a substrate. The primary interacting proteins include glycogen phosphorylase (which releases it from glycogen), UDP-glucose pyrophosphorylase (which converts it to UDP-glucose), and phosphoglucomutase (which converts it to glucose-6-phosphate). These enzymes are central to the regulation of blood sugar levels and energy storage in both animals and plants. It is a natural metabolite; thus, its "targets" are the normal metabolic pathways it feeds into. It has no intended drug target or pharmacological mechanism of action.
ln Vitro
In vitro studies involving alpha-D-Glucose-1-phosphate are centered on enzyme kinetics. It is used as a substrate to measure the activity of enzymes like UDP-glucose pyrophosphorylase. In a typical in vitro setup, the enzyme is incubated with varying concentrations of alpha-D-Glucose-1-phosphate (e.g., 0-10 mM) and UTP. The reaction produces UDP-glucose and pyrophosphate. The activity is measured via a coupled enzyme assay, where pyrophosphate is converted to inorganic phosphate, which is detected colorimetrically. The compound does not have an IC50 value; instead, it has a Km value that describes the enzyme's affinity for it. It has also been characterized as an alternative substrate for enzymes such as sucrose 3-dehydrogenase and 3-phytase.
ln Vivo
alpha-D-Glucose-1-phosphate is not a drug and has no direct therapeutic in vivo activity. However, it is a crucial molecule for in vivo glucose homeostasis. When animals are in a fasting state, glycogen stores are broken down in the liver to produce glucose. Glycogen phosphorylase cleaves glycogen to release alpha-D-Glucose-1-phosphate, which is then converted to glucose-6-phosphate and eventually free glucose. This in vivo process is essential for maintaining blood sugar levels. Its activity in animal models is measured by the concentration of the compound in liver and muscle tissues after hormonal stimulation (e.g., glucagon or insulin).
Enzyme Assay
Non-cellular (enzymatic) assays using alpha-D-Glucose-1-phosphate are standard for studying glycogen metabolism. A protocol for glycogen phosphorylase activity is performed in a 96-well plate. The reaction mixture contains 50 mM HEPES buffer (pH 7.0), 5 mM MgCl2, 1 mg/mL glycogen, 1 mM NADP+, 1 unit of phosphoglucomutase, and 1 unit of glucose-6-phosphate dehydrogenase. alpha-D-Glucose-1-phosphate (0-2 mM) is added, and the reaction is initiated by adding purified glycogen phosphorylase. The production of NADPH is measured by the increase in absorbance at 340 nm over 10-20 minutes. This assay is used to screen for potential inhibitors of glycogen metabolism for metabolic disease research.
Cell Assay
Cell-based assays for alpha-D-Glucose-1-phosphate are not common, as it is a charged metabolite that does not readily cross cell membranes. Instead, cells are treated with agents that modulate glycogen metabolism, and the levels of intracellular alpha-D-Glucose-1-phosphate are measured as a downstream biomarker. A typical protocol involves culturing hepatocytes (e.g., HepG2 cells) in glucose-free media. The cells are treated with hormones like glucagon or forskolin to activate glycogenolysis. Cells are then harvested and lysed. The lysate is deproteinized, and the concentration of alpha-D-Glucose-1-phosphate is quantified using an enzymatic cycling assay or LC-MS. This provides a measure of the cellular glycogenolytic flux, using the compound as a key endpoint metabolite.
Animal Protocol
In vivo animal experiments utilize alpha-D-Glucose-1-phosphate as a metabolic tracer. A protocol uses 8-week-old male C57BL/6 mice fasted for 4-6 hours. The mice are subjected to a pyruvate tolerance test or an insulin tolerance test. Blood glucose is measured at 0, 15, 30, 60, and 120 minutes. At the endpoint, the mice are sacrificed, and their livers are flash-frozen in liquid nitrogen. Liver samples are homogenized, and levels of alpha-D-Glucose-1-phosphate are determined by HPLC or LC-MS/MS. The concentration of this metabolite provides direct evidence of the activation or inhibition of the glycogenolysis pathway in response to the treatment. This is a standard method for studying diabetes and glycogen storage diseases.
ADME/Pharmacokinetics
alpha-D-Glucose-1-phosphate has a molecular formula of C6H13O9P and a molecular weight of 260.14 g/mol. It has a very low logP (approximately -3.8), indicating high hydrophilicity and poor cell permeability. It is generally supplied as a disodium salt (or other salt forms) to enhance solubility. It is a white crystalline powder. It is stable at 4degC for short-term storage, but for long-term storage, it should be kept at -20degC as a powder. In solution, it is stable for 6 months at -80degC. It is slightly soluble in water, and the pH of a 1% solution is typically acidic (pH ~3-4). The compound is a metabolic intermediate and is widely available as a high-purity (≥98%) biochemical reagent.
Toxicity/Toxicokinetics
alpha-D-Glucose-1-phosphate is non-toxic and is a normal, essential molecule in all living organisms. It is not classified as a hazardous chemical. However, when handling the concentrated powder, standard laboratory safety precautions should be followed, including wearing gloves and a lab coat to avoid fine dust inhalation. It is not a drug, a carcinogen, or a reproductive toxin. The compound is used as a universal standard for calibrating enzymatic assays in biochemistry. Safety Data Sheets (SDS) recommend avoiding ingestion or inhalation, but the compound poses a low acute toxicity risk. It is a product for research use only, not for human consumption.
References

[1]. 2-O-α-D-glucosylglycerol phosphorylase from Bacillus selenitireducens MLS10 possessing hydrolytic activity on β-D-glucose 1-phosphate. PLoS One. 2014 Jan 22;9(1):e86548.

Additional Infomation
Alpha-D-glucose 1-phosphate is a D-glucopyranose-1-phosphate with an α-configuration at its terminal carbon atom. Functionally, it is related to α-D-glucose. It is the conjugate acid of α-D-glucose-1-phosphate (2-). Glucose-1-phosphate is found in or produced by *Escherichia coli* (strains K12 and MG1655). Alpha-D-glucose-1-phosphate has also been reported in *Chlamydomonas reinhardtii*, *Phaseolus spp.*, and *Caenorhabditis elegans*, but relevant data are unclear. Alpha-D-glucose-1-phosphate is found in or produced by *Saccharomyces cerevisiae*.
alpha-D-Glucose-1-phosphate is a fundamental building block in the fields of biochemistry and molecular biology. It is central to the concept of "substrate-level regulation" in metabolism. Its role as a key intermediate in both glycogenesis (glycogen formation) and glycogenolysis (glycogen breakdown) makes it a critical node in the regulation of blood glucose. The discovery of this compound and its role by Earl Sutherland Jr. contributed to his Nobel Prize-winning work on the mechanisms of hormone action. Today, it is used in in vitro diagnostic kits to measure glycogen phosphorylase activity, which can be a biomarker for acute coronary syndrome and other ischemic conditions. It is not a drug, but it is essential for developing and monitoring therapies for Type 2 diabetes, where glycogen metabolism is often dysregulated.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H13O9P
Molecular Weight
260.14
Exact Mass
260.03
CAS #
59-56-3
Related CAS #
56401-20-8 (di-hydrochloride salt) ; 6736-77-2 (di-potassium salt) ; 68901-12-2 (lead salt) ; 6997-09-7 (mono-calcium salt)
PubChem CID
65533
Appearance
White to off-white solid powder
Density
1.9g/cm3
Boiling Point
603ºC at 760mmHg
Flash Point
318.5ºC
Index of Refraction
1.606
LogP
0
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
3
Heavy Atom Count
16
Complexity
277
Defined Atom Stereocenter Count
5
SMILES
OCC1OC(OP(O)(O)=O)C(O)C(O)C1O
InChi Key
HXXFSFRBOHSIMQ-VFUOTHLCSA-N
InChi Code
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
Chemical Name
[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dihydrogen phosphate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.8441 mL 19.2204 mL 38.4408 mL
5 mM 0.7688 mL 3.8441 mL 7.6882 mL
10 mM 0.3844 mL 1.9220 mL 3.8441 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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