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UDP-GlcNAc Disodium Salt

Cat No.:V28808 Purity: ≥98%
UDP-GlcNAc Disodium Salt (UDP-α-DN-Acetylglucosamine Disodium Salt) is a donor substrate for O-GlcNAc transferase (OGT).
UDP-GlcNAc Disodium Salt
UDP-GlcNAc Disodium Salt Chemical Structure CAS No.: 91183-98-1
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
UDP-GlcNAc Disodium Salt (UDP-α-DN-Acetylglucosamine Disodium Salt) is a donor substrate for O-GlcNAc transferase (OGT).
UDP-GlcNAc Disodium Salt (UDP-α-D-N-Acetylglucosamine Disodium Salt) is an essential nucleotide sugar molecule and a critical donor substrate for O-GlcNAc transferase (OGT). With a molecular formula of C17H25N3O17P2·2Na and a molecular weight of 651.32 g/mol, it is a key metabolite involved in protein glycosylation and the regulation of numerous cellular processes.
Biological Activity I Assay Protocols (From Reference)
Targets
UDP-GlcNAc targets O-GlcNAc transferase (OGT), a nucleoplasmic glycosyltransferase that adds N-acetylglucosamine residues to proteins. As the donor substrate for OGT, UDP-GlcNAc is used to modify thousands of proteins within the cytosol and nucleus. This O-GlcNAcylation is a dynamic and reversible post-translational modification that plays a crucial role in regulating cellular signaling, gene expression, and metabolism.
ln Vitro
OGT is a member of the CAZY (carbohydrate-active enzyme) database GT41 family middle and is a nucleoplasmic glycosyltransferase (uridine diphosphate-N-glycosyltransferase: acetone beta-N-glycosyltransferase or O-GlcNAc transferase). The enzyme adds distinct N-acetylglucosamine residues to the inside of the cytosol and nucleus, modifying thousands of uptake substrates using UDP-GlcNAc disodium salt (UDP-GlcNAc) as the donor substrate. protein [1].
In vitro, UDP-GlcNAc is used as a substrate in enzymatic assays to study O-GlcNAc transferase (OGT) activity. It is a critical component for in vitro glycosylation reactions, where it serves as the sugar donor for the modification of acceptor proteins. The compound is essential for studying the biochemistry of O-GlcNAcylation, including identifying OGT substrates and characterizing its enzymatic properties.
ln Vivo
In vivo, UDP-GlcNAc is a naturally occurring metabolite found in organisms ranging from bacteria to mammals. It is a biological precursor to insect chitin, muramic acid in bacterial cell walls, and sialic acid in mammalian glycoproteins. It plays a central role in the hexosamine biosynthesis pathway (HBP) and is involved in the regulation of gene expression and cellular metabolism. It is also involved in the regulation of gene expression.
Enzyme Assay
The in vitro OGT activity assay involves incubating the enzyme (OGT) with a peptide or protein substrate and UDP-GlcNAc as the sugar donor. The reaction is typically carried out in a suitable buffer at an optimal pH. The transfer of GlcNAc to the substrate is detected using various methods, including radioactive labeling (using [3H]-UDP-GlcNAc), fluorescence-based assays, or by Western blotting using an anti-O-GlcNAc antibody.
Cell Assay
In vitro cell culture studies for UDP-GlcNAc are often focused on understanding the role of O-GlcNAcylation in cellular signaling. Cells can be treated with glucosamine or other precursors to increase intracellular UDP-GlcNAc levels. Alternatively, OGT inhibitors can be used to reduce O-GlcNAcylation. The effect on protein O-GlcNAcylation is assessed by Western blotting, and downstream effects on cell signaling, gene expression, and metabolism are studied.
Animal Protocol
In vivo animal experiments for UDP-GlcNAc are not typically performed, as it is a metabolite. However, its role in metabolism can be studied by manipulating the hexosamine biosynthesis pathway in animal models. For example, administering glucosamine can increase UDP-GlcNAc levels and affect insulin sensitivity. Its role as a precursor to chitin can be studied in insect models.
ADME/Pharmacokinetics
UDP-GlcNAc Disodium Salt has a molecular formula of C17H25N3O17P2·2Na and a molecular weight of 651.32 g/mol. It is a white to off-white solid powder that is soluble in water. It is typically stored at -20°C for long-term stability. Its stability is maintained under recommended storage conditions. It is a very hygroscopic compound and should be protected from moisture.
Toxicity/Toxicokinetics
Toxicological data for UDP-GlcNAc are limited, as it is a biochemical reagent. As a naturally occurring metabolite, it is generally considered to have low toxicity. It is not intended for human therapeutic use. Standard safety precautions for handling chemical reagents should be followed.
References

[1]. Antibodies and activity measurements for the detection of O-GlcNAc transferase and assay of its substrate, UDP-GlcNAc. Methods Mol Biol. 2013;1022:147-59.

Additional Infomation
UDP-N-acetyl-α-D-glucosamine is a UDP-amino sugar whose amino sugar component is N-acetyl-α-D-glucosamine. It is a metabolite in both E. coli and mice. Functionally, it is related to UDP-D-glucosamine. It is the conjugate acid of UDP-N-acetyl-α-D-glucosamine (2-). Uriboside diphosphate-N-acetylglucosamine has been reported in Daphnia pulex, Drosophila melanogaster, and other organisms with relevant data. Uriboside diphosphate-N-acetylglucosamine is a metabolite found or produced in Saccharomyces cerevisiae. It is a biological precursor to insect chitin, muramic acid in bacterial cell walls, and sialic acid in mammalian glycoproteins.
UDP-GlcNAc Disodium Salt is a research compound with no clinical approval. It is an essential reagent for studying glycobiology, particularly the role of O-GlcNAcylation in health and disease. It is used in studies of metabolic diseases, including diabetes and cancer, where O-GlcNAcylation is dysregulated. It is also used in enzymatic studies for the synthesis of glycosaminoglycans, antibiotics, and antifungal compounds.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H25N3O17P2-2.2[NA+]
Molecular Weight
651.3175
Exact Mass
651.045
CAS #
91183-98-1
Related CAS #
UDP-GlcNAc-13C disodium
PubChem CID
445675
Appearance
White to off-white solid powder
LogP
-6.6
Hydrogen Bond Donor Count
9
Hydrogen Bond Acceptor Count
17
Rotatable Bond Count
10
Heavy Atom Count
39
Complexity
1080
Defined Atom Stereocenter Count
9
SMILES
CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)CO)O)O
InChi Key
LFTYTUAZOPRMMI-CFRASDGPSA-N
InChi Code
InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1
Chemical Name
[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen 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)
DMSO : ~250 mg/mL (~383.84 mM)
H2O : ~125 mg/mL (~191.92 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.19 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (3.19 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (3.19 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.5353 mL 7.6767 mL 15.3534 mL
5 mM 0.3071 mL 1.5353 mL 3.0707 mL
10 mM 0.1535 mL 0.7677 mL 1.5353 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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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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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