Uridine-5'-diphosphoglucose disodium salt
[CAS# 27821-45-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: Uridine-5'-diphosphoglucose disodium salt
• Synonyms: 5'-UDP-Na2
• Molecular Formula: C₉H₁₂N₂Na₂O₁₂P₂
• Molecular Weight: 448.12
• Protein Sequence: U
• CAS Registry Number: 27821-45-0
• EC Number: 248-678-9
• SMILES: C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)([O-])OP(=O)(O)[O-])O)O.[Na+].[Na+]

Properties

• Solubility: Soluble 100 mM (water) (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Uridine-5'-diphosphoglucose disodium salt is a nucleotide sugar that plays an essential role in cellular metabolism, particularly in the biosynthesis of glycogen and glycoproteins. It is a derivative of uridine, which is a nucleoside consisting of the base uracil and the sugar ribose. The disodium salt form of uridine-5'-diphosphoglucose (UDP-glucose) is a key intermediate in many biochemical pathways, acting as a glucosyl donor in the transfer of glucose units during glycosylation reactions.

The discovery of UDP-glucose dates back to the early studies of nucleotide sugars, with researchers identifying it as an important donor molecule in the synthesis of polysaccharides and glycoproteins. The molecule is formed through the phosphorylation of glucose by UDP-glucose pyrophosphorylase, which uses uridine triphosphate (UTP) and glucose-1-phosphate as substrates. This process is crucial in organisms ranging from bacteria to humans, highlighting the central role of UDP-glucose in carbohydrate metabolism.

One of the primary applications of UDP-glucose is in glycogen biosynthesis. In this process, UDP-glucose donates glucose units to growing glycogen chains, facilitated by the enzyme glycogen synthase. This is an important step in energy storage, as glycogen is a major form of glucose storage in animals, particularly in the liver and muscles. The ability of UDP-glucose to transfer glucose molecules is also crucial in other areas of carbohydrate metabolism, such as the synthesis of glycosaminoglycans and glycoproteins.

In addition to its role in glycogen synthesis, UDP-glucose is involved in the synthesis of various complex carbohydrates. For instance, it is used in the formation of cellulose in plants and the production of certain bacterial polysaccharides. The glycosylation reactions in which UDP-glucose is involved contribute to the structural diversity of glycoproteins and glycolipids, which are important for cell signaling, immune response, and the integrity of the extracellular matrix.

Another application of UDP-glucose is in the study of enzyme kinetics and metabolic pathways. Researchers often use UDP-glucose in vitro to investigate the mechanisms of glycosyltransferases, the enzymes responsible for the transfer of glucose from UDP-glucose to other substrates. This has allowed for deeper understanding of glycosylation reactions and their implications in health and disease, particularly in the context of disorders related to carbohydrate metabolism, such as glycogen storage diseases.

In the pharmaceutical industry, UDP-glucose and its derivatives are also explored for their potential therapeutic uses. For example, UDP-glucose analogs may be utilized in drug development aimed at targeting glycosylation pathways, which are often altered in various diseases, including cancer and congenital disorders of glycosylation. These analogs can inhibit glycosyltransferases, potentially providing a way to modulate glycosylation in diseased cells.

The development of methods to synthesize and purify UDP-glucose has also expanded its use in various biotechnological applications. Its role as a glucosyl donor in enzymatic reactions makes it valuable in the production of bioactive compounds, such as glycosylated flavonoids or other therapeutic molecules. The growing interest in glycosylation as a therapeutic target further underscores the significance of UDP-glucose in both basic research and applied biotechnology.

In conclusion, Uridine-5'-diphosphoglucose disodium salt is a vital biochemical compound with broad applications in metabolic research, drug development, and the synthesis of complex carbohydrates. Its central role in glycosylation and carbohydrate metabolism continues to make it an essential molecule for a variety of scientific and industrial applications.

References

2022. A fluorescent sensor for real-time measurement of extracellular oxytocin dynamics in the brain. Nature Methods.
DOI: 10.1038/s41592-022-01597-x

2015. Assessment of the Efficacy of Nucleotide Therapy after Sciatic Nerve Injury. Neuroscience and Behavioral Physiology.
DOI: 10.1007/s11055-015-0149-x