91183-98-1

Basic information

• Product Name: UDP-ALPHA-D-N-ACETYLGLUCOSAMINE, DISODIUM SALT
• Synonyms: UDPAG;UDPAG SODIUM SALT;UDP-ALPHA-D-ACETYLGLUCOSAMINE, DISODIUM SALT;UDP-ALPHA-D-N-ACETYL-GLUCOSAMINE;UDP-ALPHA-D-N-ACETYLGLUCOSAMINE, DISODIUM SALT;UDP-GLCNAC, 2NA;UDP-GLCNAC, NA2;UDP-N-ACETYLGLUCOSAMINE DISODIUM SALT
• CAS NO: 91183-98-1
• Molecular Formula: C₁₇H₂₅N₃O₁₇P₂*2Na
• Molecular Weight: 651.32
• EINECS: 293-820-5
• Mol File: 91183-98-1.mol

Chemical Properties

• Appearance: WHITE POWDER
• Storage Temp.: −20°C
• CAS DataBase Reference: UDP-ALPHA-D-N-ACETYLGLUCOSAMINE, DISODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: UDP-ALPHA-D-N-ACETYLGLUCOSAMINE, DISODIUM SALT(91183-98-1)
• EPA Substance Registry System: UDP-ALPHA-D-N-ACETYLGLUCOSAMINE, DISODIUM SALT(91183-98-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-26-36
• WGK Germany: 3
• Hazardous Substances Data: 91183-98-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
UDP-ALPHA-D-N-ACETYLGLUCOSAMINE, DISODIUM SALT is used as a chemical reagent in studies relating to the synthesis of immunogens. It aids in understanding the mechanisms of immune responses and the development of vaccines and therapeutic agents.
Used in Enzyme Activity Assays:
As a GlcNAc transferase substrate, UDP-ALPHA-D-N-ACETYLGLUCOSAMINE, DISODIUM SALT is utilized in assays to evaluate the activity of enzymes involved in the transfer of N-acetylglucosamine residues to proteins and other molecules. This helps in studying the role of these enzymes in various biological processes and their potential as therapeutic targets.
Used in Endoplasmic Reticulum to Golgi Transport Assay:
In this application, UDP-ALPHA-D-N-ACETYLGLUCOSAMINE, DISODIUM SALT serves as a component of the reaction cocktail, enabling researchers to investigate the transport mechanisms of proteins and lipids between the endoplasmic reticulum and Golgi apparatus. This knowledge is essential for understanding cellular functions and the development of targeted therapies.
Used in Quantification of UDP-GlcNAc in Liver Tissues:
As a reference standard, UDP-ALPHA-D-N-ACETYLGLUCOSAMINE, DISODIUM SALT is employed in high-performance liquid chromatography (HPLC) to quantify UDP-GlcNAc levels in liver tissues. This helps in assessing the metabolic status of the liver and the involvement of UDP-GlcNAc in various liver diseases.
Used in Testing the Glycosylation Activity of O-GlcNAc Transferase (OGT):
UDP-ALPHA-D-N-ACETYLGLUCOSAMINE, DISODIUM SALT is used to evaluate the glycosylation activity of OGT against peptide substrates. This is crucial for understanding the role of OGT in the regulation of protein function and its implications in various diseases, including diabetes and neurodegenerative disorders.

Biochem/physiol Actions

Uridine 5′-diphospho-N-acetylglucosamine (UDP-GlcNAc) is a sugar donor and aids in the endomembrane glycosylation of endoplasmic reticulum and Golgi. The decreased levels of UDP-GlcNAc has an influence on the normal cellular proliferation and apoptosis. UDP-GlcNAc elicits feedback inhibition of the enzyme glutamine:fructose-6-phosphate amidotransferase (GFAT).

Upstream product

• 1355005-35-4 2-azido-2-deoxy-D-glucopyranose-3,4,6-triacetate-1-(dihydrogen phosphate) 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 171032-74-9 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose 
• 63-39-8 UTP 
• 1476-50-2 uridine 5'-triphosphate trisodium salt 

Downstream Products

• 1079925-74-8 N-acetylglucosaminylribostamycin 
• 58-98-0 UDP 
• 1042435-73-3 2-N-(benzyloxycarbonyl)-aminoethyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2->3)-[2-acetamido-2-deoxy-O-β-D-galactopyranosyl-(1->4)]-O-(β-D-galactopyranosyl)-(1->4)-O-β-D-glucopyranoside 

Relevant articles and documents

Chemoenzymatic synthesis of uridine diphosphate-GlcNAc and uridine diphosphate-GalNAc analogs for the preparation of unnatural glycosaminoglycans

Eight N-acetylglucosamine-1-phosphate and N-acetylgalactosamine-1-phosphate analogs have been synthesized chemically and were tested for their recognition by the GlmU uridyltransferase enzyme. Among these, only substrates that have an amide linkage to the C-2 nitrogen were transferred by GlmU to afford their corresponding uridine diphosphate(UDP)-sugar nucleotides. Resin-immobilized GlmU showed comparable activity to nonimmobilized GlmU and provides a more facile final step in the synthesis of an unnatural UDP-donor. The synthesized unnatural UDP-donors were tested for their activity as substrates for glycosyltransferases in the preparation of unnatural glycosaminoglycans in vitro. A subset of these analogs was useful as donors, increasing the synthetic repertoire for these medically important polysaccharides.

Synthesis of sugar nucleotides by application of phosphoramidites

(Chemical Equation Presented) A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate-phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.

Gram-Scale Synthesis of Uridine 5'-Diphospho-N-acetylglucosamine: Comparison of Enzymatic and Chemical Routes

Practical chemoenzymatic and chemical routes to uridine 5'-diphospho-N-acetylglucosamine (UDP-GlcNAc) on a gram scale have been developed.The chemoenzymatic synthesis provided convenient access to glucosamine-6-phosphate and N-acetylglucosamine-6-phosphate (GlcNAc-6-P) in > 10 mmol quantities.The condensation between GlcNAc-6-P and UTP was catalyzed by readily available crude enzyme extract from dried cells of the yeast Candida utilis and afforded a 17 percent yield of UDP-GlcNAc from GlcNAc-6-P.The otherwise straightforward chemoenzymatic sequence was hampered by the need to purify the product from the final complex reaction mixture.The chemical synthesis of UDP-GlcNAc proceeded through five steps in an overall yield of 15 percent from pentaacetylglucosamine with the selective formation of tetraacetylglucosamine-α-1-phosphate as the key reaction.