dTDP-L-Rha

Synonyms dTDP-6-deoxy-β-L-mannose dTDP-L-rhamnose dTDP-L-Rha SMILES CC1(\C(=O)NC(N(\C=1)[C@H]3(C[C@H](O)[C@@H](COP(=O)([O-])OP(O[C@H]2(O[C@@H](C)[C@H](O)[C@@H](O)[C@@H](O)2))(=O)[O-])O3))=O) InChI InChI=1S/C16H26N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-13,15,19-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/p-2/t7-,8-,9+,10+,11-,12+,13+,15+/m0/s1 InChIKey InChIKey=ZOSQFDVXNQFKBY-CGAXJHMRSA-L dTDP-L-Rha (dTDP-L-rhamnose) is a nucleotide sugar composed of thymidine diphosphate (dTDP) and L-rhamnose, a six-carbon deoxy sugar. dTDP-L-Rha is a critical building block in the biosynthesis of various glycans, including polysaccharides, glycoproteins, and glycolipids, particularly in bacterial and plant systems. Structure & Properties: Molecular Weight (MW): Approximately 546 g/mol (depending on specific substitutions) Chemical Formula: C16H26N2O15P2 Synonyms: dTDP-L-rhamnose, thymidine diphospho-L-rhamnose Functional Groups: Characterized by a deoxy sugar (L-rhamnose) lacking a hydroxyl group at the 6-position. Biological Role: Biosynthesis Pathway: dTDP-L-Rha is synthesized from glucose-1-phosphate via a series of enzymatic reactions that transform dTDP-D-glucose into dTDP-L-rhamnose. This conversion includes epimerization and reduction steps. Function: dTDP-L-Rha serves as a sugar donor in glycosylation reactions, contributing to the formation of rhamnose-containing glycans. These glycans are key components in bacterial cell walls and plant cell structures. Applications: Bacterial Glycobiology: dTDP-L-Rha is essential in the construction of bacterial surface structures, such as lipopolysaccharides (LPS), capsules, and exopolysaccharides, which are critical for bacterial virulence and immune system evasion. Plant Glycobiology: It is also involved in the formation of pectin and other polysaccharides in plant cell walls, playing a role in plant growth and development. Significance in Research: Pathogen Glycan Diversity: dTDP-L-Rha contributes to the structural diversity of glycans, particularly in pathogens, influencing their ability to evade the host immune system. Therapeutic Targeting: Understanding the biosynthesis of dTDP-L-Rha is important for developing antibacterial therapies, especially those targeting bacterial cell wall components. Key Roles: Lipopolysaccharide (LPS) Biosynthesis: dTDP-L-Rha is a critical sugar in the LPS of Gram-negative bacteria, which are major virulence factors contributing to pathogenicity. Capsule and Exopolysaccharide Biosynthesis: It is also involved in the formation of bacterial capsules and biofilms, which protect bacteria from environmental stresses and antibiotics. Storage and Stability: Storage: dTDP-L-Rha should be stored at -20°C in a moisture-free environment for optimal stability. Stability: The compound remains stable under these storage conditions but may degrade when exposed to heat, moisture, or light. Research Applications: Glycan Engineering: dTDP-L-Rha is used in research to synthesize rhamnose-containing glycan structures for studying bacterial virulence, immune responses, and plant cell wall biosynthesis. Vaccine and Drug Development: The role of dTDP-L-Rha in bacterial glycobiology makes it a target for developing vaccines and antimicrobial agents aimed at preventing bacterial infections. Potential Impact: Antibacterial Strategies: By targeting the enzymes responsible for dTDP-L-Rha biosynthesis, new antibacterial strategies can be developed that disrupt the integrity of bacterial cell walls. Synthetic Glycans: dTDP-L-Rha is useful in creating synthetic glycan structures for therapeutic or diagnostic purposes, particularly in bacterial glycan research. Key Research Areas: Bacterial Virulence and Immune Evasion: dTDP-L-Rha-containing glycans are involved in bacterial evasion of the immune system, making them a focus for developing immune-modulating therapies. Enzyme Inhibition: Research on the enzymes responsible for generating dTDP-L-Rha can lead to the development of inhibitors that prevent the synthesis of crucial bacterial glycans. Conclusion: dTDP-L-Rha (dTDP-L-rhamnose) is a critical nucleotide sugar involved in the biosynthesis of complex bacterial and plant glycans. Its importance in bacterial survival, virulence, and immune evasion makes it a valuable target for antibacterial research and therapeutic development. Additionally, it is a versatile molecule in synthetic biology for creating novel glycan structures, with potential applications in research and medicine.