dTDP-Qui4N

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Chemical FormulaC16H26N3O14P2

 

Molecular Weight546.34 Daltons
Monoisotopic Mass547.0968256117 Daltons
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SynonymsdTDP-4-amino-4,6-dideoxy-α-D-glucopyranose
dTDP-4-amino-4,6-dideoxy-α-D-glucose
dTDP-Qui4N
SMILESCC1(\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]([NH3+])[C@H](O)[C@@H](O)2))(=O)[O-])O3))=O)
InChIInChI=1S/C16H27N3O14P2/c1-6-4-19(16(24)18-14(6)23)10-3-8(20)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(17)7(2)30-15/h4,7-13,15,20-22H,3,5,17H2,1-2H3,(H,25,26)(H,27,28)(H,18,23,24)/p-1/t7-,8+,9-,10-,11-,12+,13-,15-/m1/s1
InChIKeyInChIKey=UIVJXHWSIFBBCY-LPGAPTBISA-M

dTDP-Qui4N (dTDP-4-amino-4,6-dideoxy-α-D-glucose) is a nucleotide sugar that plays an essential role in bacterial glycosylation. It is involved in the biosynthesis of complex carbohydrates, including cell surface polysaccharides, lipopolysaccharides (LPS), and other glycoconjugates that contribute to the structure and virulence of bacterial cells.

Structure & Properties:

  • Molecular Weight (MW): Approximately 547 g/mol
  • Chemical Formula: C16H26N3O13P2
  • Synonyms: dTDP-4-amino-4,6-dideoxy-α-D-glucose, dTDP-Qui4N
  • Functional Groups: This compound features an amino group at the 4-position and lacks hydroxyl groups at the 4 and 6 positions, which differentiates it from other sugars like glucose.

Biological Role:

  • Biosynthesis Pathway: dTDP-Qui4N is synthesized through a series of enzymatic reactions from dTDP-glucose. It serves as an activated glycosyl donor in glycosylation reactions.
  • Function: It is used by various bacterial glycosyltransferases to incorporate 4-amino-4,6-dideoxy sugars into glycan structures, contributing to the formation of bacterial cell walls and virulence factors.

Applications:

  1. Bacterial Glycobiology: dTDP-Qui4N is essential for the biosynthesis of bacterial surface polysaccharides, particularly in pathogens, where it contributes to the formation of antigenic determinants.
  2. Enzyme Studies: It is commonly used in research on enzymes that catalyze the transfer of dideoxy sugar moieties in bacterial cells.

Significance in Research:

  1. Pathogen Interaction: dTDP-Qui4N is involved in the construction of LPS and other bacterial surface molecules that mediate pathogen interactions with the host immune system, making it a critical molecule for studying host-pathogen dynamics.
  2. Structural Diversity: By providing dideoxy amino sugars for glycosylation, dTDP-Qui4N increases the structural diversity of bacterial glycan assemblies, impacting bacterial fitness, immune evasion, and pathogenicity.

Key Roles:

  • Polysaccharide Biosynthesis: dTDP-Qui4N is incorporated into polysaccharides that contribute to the protective cell walls of bacteria, particularly those involved in biofilm formation and resistance to host defenses.
  • Virulence Factor: The inclusion of Qui4N in bacterial glycans can enhance the virulence of pathogens by altering the immunogenic properties of their surface structures.

Storage and Stability:

  • Storage: Store at -20°C in a dry, sealed container to prevent moisture degradation.
  • Stability: Stable when stored under recommended conditions; however, exposure to moisture and heat can lead to degradation.

Research Applications:

  1. Antimicrobial Research: Targeting the biosynthesis of dTDP-Qui4N could lead to novel antimicrobial strategies by inhibiting the production of essential bacterial surface molecules.
  2. Vaccine Development: By understanding how dTDP-Qui4N is integrated into bacterial glycans, researchers can develop vaccines that target key glycan structures in pathogens.

Potential Impact:

  • Therapeutic Targeting: Disrupting the biosynthesis or function of dTDP-Qui4N in bacteria could impair their ability to construct protective glycans, making them more susceptible to immune responses or antibiotics.
  • Immune Response Modulation: Modifying the synthesis of dTDP-Qui4N-containing polysaccharides may alter the bacterial interaction with the host’s immune system, providing potential pathways for immune modulation or vaccine enhancement.

dTDP-Qui4N is a vital nucleotide sugar involved in bacterial polysaccharide biosynthesis, influencing the structure, virulence, and immune evasion mechanisms of many pathogenic bacteria. Understanding its role and function offers significant insights for developing new antimicrobial therapies and vaccines

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Size

15 MG, 25 MG, 5 MG

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