UDP-4n-D-QuiNAc

Synonyms UDP-6-deoxy- N - acetyl-α-D-glucosamine UDP-D-QuiNAc UDP-QuiNAc SMILES C[C@@H]3([C@@H](O)[C@@H]([C@H]([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-])O3)NC(C)=O)O) InChI InChI=1S/C17H27N3O16P2/c1-6-11(23)13(25)10(18-7(2)21)16(33-6)35-38(30,31)36-37(28,29)32-5-8-12(24)14(26)15(34-8)20-4-3-9(22)19-17(20)27/h3-4,6,8,10-16,23-26H,5H2,1-2H3,(H,18,21)(H,28,29)(H,30,31)(H,19,22,27)/p-2/t6-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1 InChIKey InChIKey=INJACODUUNZJCO-WNSRFTAOSA-L UDP-4N-D-QuiNAc (Uridine Diphosphate 4-Amino-4-Deoxy-N-acetyl-D-quinovose) is a nucleotide sugar involved in bacterial glycan biosynthesis. It consists of uridine diphosphate (UDP) linked to a modified sugar, 4-amino-4-deoxy-N-acetyl-D-quinovose (QuiNAc), which plays a role in the formation of complex glycan structures. Structure & Properties: Molecular Weight (MW): Approximately 569 g/mol (depending on specific form and substitutions) Chemical Formula: C17H28N3O16P2 (approximate) Synonyms: UDP-4-amino-4-deoxy-N-acetylquinovose Functional Groups: The molecule features an amino group at the 4-position and an N-acetyl group on the sugar ring, which distinguishes it from other nucleotide sugars. Biological Role: Biosynthesis Pathway: UDP-4N-D-QuiNAc is synthesized through a series of enzymatic steps that involve the conversion of common sugars like UDP-glucose into this specialized sugar nucleotide, which is used as a glycosyl donor. Function: It plays a crucial role in transferring the 4N-D-QuiNAc residue to acceptor molecules in the biosynthesis of bacterial polysaccharides, which are essential for cell wall integrity and virulence in certain bacteria. Applications: Bacterial Glycosylation: UDP-4N-D-QuiNAc is involved in glycosylation processes in bacteria, contributing to the formation of glycoproteins and glycolipids that are important for bacterial survival and pathogenicity. Synthetic Biology: This molecule can be used in synthetic biology to produce engineered glycans for therapeutic and industrial purposes. Significance in Research: Bacterial Glycan Diversity: The presence of rare sugars like 4N-D-QuiNAc in bacterial glycans adds to the diversity of bacterial glycosylation, influencing their interactions with host organisms and immune systems. Therapeutic Targeting: Studying the biosynthesis and function of UDP-4N-D-QuiNAc provides insights that could be used to develop new antibacterial treatments that disrupt glycan formation in pathogenic bacteria. Key Roles: Bacterial Virulence: UDP-4N-D-QuiNAc is important for the synthesis of bacterial surface glycans, which can contribute to virulence and immune evasion in pathogenic bacteria. Cell Wall Synthesis: This molecule is involved in the formation of bacterial cell wall components that are essential for maintaining cell shape and structural integrity. Storage and Stability: Storage: UDP-4N-D-QuiNAc should be stored at -20°C in a moisture-free environment to maintain its stability. Stability: The compound remains stable under these conditions but may degrade when exposed to heat, moisture, or light. Research Applications: Glycobiology: UDP-4N-D-QuiNAc is used to study bacterial glycan biosynthesis and the role of modified sugars in glycosylation pathways. Biotechnology: This nucleotide sugar is useful for engineering bacteria or other systems to produce modified glycan structures for therapeutic or research applications. Potential Impact: Antibacterial Strategies: Targeting the biosynthesis of UDP-4N-D-QuiNAc in pathogenic bacteria could help weaken their defenses, making them more susceptible to immune responses or antibacterial agents. Synthetic Glycan Development: Engineering synthetic glycans containing 4N-D-QuiNAc could lead to the development of new biomaterials or therapeutic compounds with specific biological functions. Key Research Areas: Bacterial Pathogenesis: Understanding the role of UDP-4N-D-QuiNAc in glycan biosynthesis could lead to advances in the study of bacterial pathogenesis and immune evasion. Glycan Engineering: Research into UDP-4N-D-QuiNAc supports the development of novel glycan structures with potential applications in biotechnology, medicine, and vaccine development. Conclusion: UDP-4N-D-QuiNAc is a unique nucleotide sugar that plays a vital role in bacterial glycan biosynthesis. Its involvement in glycosylation processes makes it a key molecule for research into bacterial pathogenicity, synthetic biology, and the development of antibacterial strategies. The ability to manipulate and study glycans containing 4N-D-QuiNAc opens new avenues for therapeutic and industrial applications.