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N-Acetyl-α-D-glucosamine 1-phosphate disodium

Cat No.:V45539 Purity: ≥98%
N-acetyl-α-d-glucosamine 1-phosphate disodium (GlcNAc-1-P) is an ectopic sugar phosphate and a key intermediate in N-glycoprotein biosynthesis.
N-Acetyl-α-D-glucosamine 1-phosphate disodium
N-Acetyl-α-D-glucosamine 1-phosphate disodium Chemical Structure CAS No.: 31281-59-1
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
N-acetyl-α-d-glucosamine 1-phosphate disodium (GlcNAc-1-P) is an ectopic sugar phosphate and a key intermediate in N-glycoprotein biosynthesis. N-acetyl-α-d-glucosamine 1-phosphate disodium is a metabolic precursor of the bacterial cell wall components phosphocholic acid and ratamine.
N-Acetyl-α-D-glucosamine 1-phosphate disodium salt is a phosphorylated sugar nucleotide precursor and a key intermediate in the biosynthesis of glycosaminoglycans and glycoproteins. It has the molecular formula C₈H₁₄NNa₂O₉P and a molecular weight of 357.14. The compound is a derivative of N-acetylglucosamine (GlcNAc) with a phosphate group at the 1-position. It is used in research on glycosaminoglycan biosynthesis, bacterial cell wall synthesis, and glycobiology. N-Acetyl-α-D-glucosamine 1-phosphate is a substrate for the enzyme UDP-N-acetylglucosamine pyrophosphorylase, which catalyzes the formation of UDP-GlcNAc.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary target of N-Acetyl-α-D-glucosamine 1-phosphate is the enzyme UDP-N-acetylglucosamine pyrophosphorylase (also known as GlmU or UAP1). This enzyme catalyzes the conversion of N-acetyl-α-D-glucosamine 1-phosphate and UTP to UDP-N-acetylglucosamine (UDP-GlcNAc) and pyrophosphate. UDP-GlcNAc is a critical sugar nucleotide donor for the biosynthesis of glycosaminoglycans, glycoproteins, and bacterial cell wall components. By serving as a substrate for this enzyme, N-Acetyl-α-D-glucosamine 1-phosphate plays a key role in glycobiology and cellular metabolism.
ln Vitro
In vitro, N-Acetyl-α-D-glucosamine 1-phosphate serves as a substrate for UDP-N-acetylglucosamine pyrophosphorylase. In enzyme activity assays, the compound is incubated with the enzyme, UTP, and appropriate cofactors, and the production of UDP-GlcNAc is measured. The compound's activity as a substrate can be assessed by measuring the rate of UDP-GlcNAc formation using HPLC, mass spectrometry, or coupled enzyme assays. The compound does not exhibit pharmacological activity; its utility is as a biochemical reagent for studying glycosylation pathways.
ln Vivo
N-Acetyl-α-D-glucosamine 1-phosphate does not have in vivo pharmacological activity. It is a biochemical reagent used for research applications, primarily in vitro, to study glycosylation pathways and enzyme mechanisms. The compound is not administered to animals for therapeutic or pharmacological studies. Its use is limited to research applications in glycobiology and biochemistry.
Enzyme Assay
Non-cellular assays for N-Acetyl-α-D-glucosamine 1-phosphate typically involve measuring its activity as a substrate for UDP-N-acetylglucosamine pyrophosphorylase. In a typical assay, the compound is incubated with the enzyme, UTP, and magnesium ions (as a cofactor) in an appropriate buffer. The reaction is allowed to proceed for a defined time, and the production of UDP-GlcNAc is measured by HPLC or by using a coupled enzyme assay with a colorimetric or fluorometric detection system. The kinetic parameters (Km, Vmax) of the enzyme for the substrate can be determined.
Cell Assay
In vitro cellular assays for N-Acetyl-α-D-glucosamine 1-phosphate are not typically conducted for pharmacological evaluation. The compound may be used in cell culture experiments to study glycosylation pathways or to supplement cells with a precursor for glycosaminoglycan biosynthesis. However, the compound is membrane-impermeant and would need to be delivered to cells using specialized methods. Its primary use is as a biochemical reagent for in vitro enzyme assays.
Animal Protocol
N-Acetyl-α-D-glucosamine 1-phosphate is not used in in vivo animal studies as a therapeutic or pharmacological agent. Its application is limited to in vitro research applications in glycobiology and biochemistry. The compound is not administered to animals for therapeutic or pharmacological studies.
ADME/Pharmacokinetics
N-Acetyl-α-D-glucosamine 1-phosphate is not a drug and does not have pharmacokinetic properties. Its physical and chemical properties are more relevant: it is a phosphorylated sugar nucleotide precursor with a molecular weight of 357.14 and a molecular formula of C₈H₁₄NNa₂O₉P. The compound is soluble in water and is typically prepared as an aqueous solution for use in enzyme assays.
Toxicity/Toxicokinetics
Specific toxicological data for N-Acetyl-α-D-glucosamine 1-phosphate are not extensively detailed in standard product information. As a biochemical reagent, it is generally considered to have low toxicity. The compound is a phosphorylated sugar and is expected to be biocompatible. However, standard laboratory safety precautions should be observed when handling this compound. It is not intended for human use.
References

[1]. A concise synthesis of C-glycosyl phosphate and phosphonate analogues of N-acetyl-α-d-glucosamine 1-phosphate. Tetrahedron Letters. 19 February 2000,41(18):1187-1189.

Additional Infomation
N-Acetyl-α-D-glucosamine 1-phosphate is a research-grade biochemical reagent intended for laboratory use only and is not approved for clinical use. Its CAS number is 31281-59-1. The primary applications of N-Acetyl-α-D-glucosamine 1-phosphate include studying the biosynthesis of glycosaminoglycans and glycoproteins, investigating bacterial cell wall synthesis, and serving as a substrate for UDP-N-acetylglucosamine pyrophosphorylase in enzyme assays. The compound is a valuable tool for glycobiology, biochemistry, and drug discovery research.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H15NNAO9P
Molecular Weight
323.17000
Exact Mass
323.038
CAS #
31281-59-1
PubChem CID
16218869
Appearance
White to off-white solid powder
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
4
Heavy Atom Count
20
Complexity
371
Defined Atom Stereocenter Count
0
SMILES
CC(=O)NC1C(C(C(OC1OP(=O)(O)O)CO)O)O.[Na]
InChi Key
ODFFMCFQIMTMQR-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H16NO9P.Na/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16;/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16);
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

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
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)
H2O : ~250 mg/mL (~724.32 mM)
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 3.0943 mL 15.4717 mL 30.9435 mL
5 mM 0.6189 mL 3.0943 mL 6.1887 mL
10 mM 0.3094 mL 1.5472 mL 3.0943 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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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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