Synonyms | dTDP-3-acetamido-3,6-dideoxy-α-D-galactopyranose
dTDP-3-N-acetyl-α-D-fucosamine
dTDP-3-acetamido-3,6-dideoxy-α-D-galactose
dTDP-D-Fuc3NAc
dTDP-3-acetamido-α-D-fucose
dTDP-Fuc3NAc |
---|
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](NC(=O)C)[C@@H](O)2))(=O)[O-])O3))=O) |
---|
InChI | InChI=1S/C18H29N3O15P2/c1-7-5-21(18(27)20-16(7)26)12-4-10(23)11(34-12)6-32-37(28,29)36-38(30,31)35-17-15(25)13(19-9(3)22)14(24)8(2)33-17/h5,8,10-15,17,23-25H,4,6H2,1-3H3,(H,19,22)(H,28,29)(H,30,31)(H,20,26,27)/p-2/t8-,10+,11-,12-,13+,14+,15-,17-/m1/s1 |
---|
InChIKey | InChIKey=CWQDRZJUANNJKC-HYPDDMKDSA-L |
---|
dTDP-Fuc3NAc (dTDP-3-acetamido-3,6-dideoxy-L-fucose) is a nucleotide sugar derivative that is part of the bacterial glycosylation pathway. It contributes to the synthesis of complex polysaccharides in bacterial systems, particularly in the formation of surface glycans and other structures involved in bacterial virulence.
Structure & Properties:
- Molecular Weight (MW): Approximately 547 g/mol
- Chemical Formula: C17H28N3O14P2S
- Synonyms: dTDP-3-acetamido-3,6-dideoxy-L-fucose, dTDP-Fuc3NAc, dTDP-3-amino-3,6-dideoxy-L-fucose
- Functional Groups: Contains an acetamido group at the 3-position and a dideoxy modification at the 6-position, along with a thymidine diphosphate moiety.
Biological Role:
- Biosynthesis Pathway: dTDP-Fuc3NAc is synthesized from dTDP-3-amino-3,6-dideoxy-L-fucose through acetylation at the 3-position. It acts as an activated donor in the biosynthesis of bacterial polysaccharides.
- Function: This nucleotide sugar is used by glycosyltransferases to incorporate fucose derivatives into bacterial glycans, which play crucial roles in cell wall structure, immune evasion, and bacterial adhesion.
Applications:
- Bacterial Glycobiology: dTDP-Fuc3NAc is essential for the biosynthesis of bacterial surface polysaccharides, such as lipopolysaccharides (LPS) and other cell surface glycans.
- Enzyme Studies: dTDP-Fuc3NAc is used to study enzymes involved in bacterial glycosylation, particularly those responsible for transferring fucose-containing sugars to glycans.
Significance in Research:
- Pathogen Interaction: dTDP-Fuc3NAc contributes to the synthesis of polysaccharides that pathogens use to interact with host immune cells, making it important in the study of pathogen-host interactions.
- Structural Diversity: The incorporation of dTDP-Fuc3NAc into bacterial glycans increases the diversity of bacterial surface structures, impacting their ability to evade immune detection and establish infections.
Key Roles:
- Polysaccharide Biosynthesis: dTDP-Fuc3NAc serves as a glycosyl donor for the assembly of bacterial glycans, including those involved in the formation of protective polysaccharide capsules and biofilms.
- Virulence Factor: Polysaccharides derived from dTDP-Fuc3NAc are often involved in bacterial virulence, contributing to immune evasion and enhancing bacterial persistence within a host.
Storage and Stability:
- Storage: Store at -20°C in a sealed container to prevent moisture absorption and degradation.
- Stability: The compound is stable when stored under appropriate conditions but should be kept dry and protected from light.
Research Applications:
- Antimicrobial Research: Targeting the biosynthetic pathway of dTDP-Fuc3NAc may lead to the development of novel antibiotics that inhibit bacterial glycan synthesis.
- Vaccine Development: Insights into dTDP-Fuc3NAc biosynthesis can contribute to the development of vaccines targeting bacterial pathogens that rely on fucose-containing glycans for virulence.
Potential Impact:
- Therapeutic Targeting: dTDP-Fuc3NAc biosynthesis and its incorporation into bacterial glycans offer potential therapeutic targets for disrupting key bacterial processes, such as immune evasion and adhesion.
- Immune Response Modulation: Modulating the synthesis of dTDP-Fuc3NAc-containing glycans may influence bacterial interactions with the host immune system, providing new avenues for enhancing immune responses against infections.
dTDP-Fuc3NAc is a vital molecule in bacterial glycan biosynthesis, contributing to the formation of polysaccharides that are essential for bacterial survival and virulence. Understanding its role in glycosylation pathways offers promising directions for antimicrobial research and vaccine development.
Reviews
There are no reviews yet.