UDP-D-GlcNAcA

Synonyms UDP-2-acetamido-2-deoxy-α-D-glucuronate UDP- N -acetyl-D-glucosaminuronate UDP- N -acetyl-2-amino-2-deoxy-α-D-glucuronate UDP-GlcNAcA UDP- N -acetylglucosaminuronic acid UDP- N -acetyl-D-glucosaminuronic acid UDP- N -acetyl-α-D-glucosaminuronic acid SMILES CC(N[C@H]3([C@@H](OP(OP(OC[C@@H]2([C@H]([C@H]([C@H](N1(\C=C/C(=O)NC1=O))O2)O)O))(=O)[O-])(=O)[O-])O[C@@H]([C@H]([C@@H]3O)O)C([O-])=O))=O InChI InChI=1S/C17H25N3O18P2/c1-5(21)18-8-10(24)11(25)13(15(27)28)36-16(8)37-40(32,33)38-39(30,31)34-4-6-9(23)12(26)14(35-6)20-3-2-7(22)19-17(20)29/h2-3,6,8-14,16,23-26H,4H2,1H3,(H,18,21)(H,27,28)(H,30,31)(H,32,33)(H,19,22,29)/p-3/t6-,8-,9-,10-,11+,12-,13+,14-,16-/m1/s1 InChIKey InChIKey=DZOGQXKQLXAPND-HHKCBAECSA-K UDP-D-GlcNAcA (Uridine Diphosphate N-Acetylglucosaminuronic Acid) is a nucleotide sugar involved in the biosynthesis of complex carbohydrates, including glycans and polysaccharides. This molecule consists of uridine diphosphate (UDP) linked to N-acetylglucosaminuronic acid (GlcNAcA), a derivative of glucosamine that features both acetyl and uronic acid modifications. Structure & Properties: Molecular Weight (MW): Approximately 619 g/mol (depending on specific form and substitutions) Chemical Formula: C17H25N3O18P2 (approximate) Synonyms: UDP-N-acetylglucosaminuronic acid Functional Groups: GlcNAcA contains an acetyl group at the nitrogen atom of the glucosamine and a carboxyl group (-COOH) at the 6-position, classifying it as a uronic acid. Biological Role: Biosynthesis Pathway: UDP-D-GlcNAcA is synthesized through a series of enzymatic reactions from UDP-GlcNAc or other sugar nucleotides. It serves as a glycosyl donor in various biosynthetic pathways. Function: This nucleotide sugar participates in the construction of glycan and polysaccharide structures in bacterial and eukaryotic systems. It is crucial for the assembly of structural and signaling molecules. Applications: Glycan Biosynthesis: UDP-D-GlcNAcA is a precursor for the synthesis of glycan structures found in cell walls, extracellular matrices, and glycoproteins. Bacterial Glycobiology: In bacteria, UDP-D-GlcNAcA contributes to the formation of surface polysaccharides, such as lipopolysaccharides (LPS), which play a role in bacterial virulence and immune interactions. Significance in Research: Polysaccharide Assembly: UDP-D-GlcNAcA is involved in the biosynthesis of polysaccharides that contribute to structural integrity and signaling within cells and tissues. Glycosylation Disorders: Disruptions in the biosynthesis or utilization of UDP-D-GlcNAcA can lead to glycosylation disorders, affecting various biological processes, including immunity, development, and cellular communication. Key Roles: Extracellular Matrix: UDP-D-GlcNAcA is a crucial building block for the biosynthesis of glycosaminoglycans (GAGs) in the extracellular matrix, which is important for tissue structure and function. Bacterial Glycans: In bacterial species, it plays a key role in constructing surface glycan structures that help in host immune evasion and bacterial survival. Storage and Stability: Storage: UDP-D-GlcNAcA should be stored at -20°C in a moisture-free environment for optimal stability. Stability: The compound is stable under these conditions but may degrade if exposed to heat, moisture, or light. Research Applications: Glycobiology: UDP-D-GlcNAcA is used in research focused on glycan biosynthesis and its role in cellular processes, such as development, signaling, and immune responses. Vaccine Development: As a component of bacterial glycan biosynthesis, UDP-D-GlcNAcA is a target for developing vaccines against pathogens that rely on glycosylated surface structures for virulence. Potential Impact: Therapeutic Targeting: Understanding the biosynthesis and function of UDP-D-GlcNAcA can help identify potential therapeutic targets for diseases associated with glycosylation defects or bacterial infections. Synthetic Biology: UDP-D-GlcNAcA is used in synthetic biology to engineer cells for the production of complex glycans, with potential applications in medicine and biotechnology. Key Research Areas: Bacterial Glycobiology: Research into UDP-D-GlcNAcA's role in bacterial glycan biosynthesis can inform the development of new antimicrobial strategies. Glycosylation Disorders: Investigating how disruptions in UDP-D-GlcNAcA biosynthesis affect glycosylation can lead to insights into related diseases and their treatment. Conclusion: UDP-D-GlcNAcA is a critical nucleotide sugar involved in glycan and polysaccharide biosynthesis, playing essential roles in both bacterial and eukaryotic systems. Its importance in cellular processes, such as glycosylation and structural integrity, makes it a valuable molecule for research into bacterial pathogenesis, therapeutic development, and glycobiology.