dTDP-Qui3NAc

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Chemical FormulaC18H27N3O15P2

 

 

Molecular Weight587.37 Daltons
Monoisotopic Mass589.1073902979999 Daltons
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SynonymsdTDP-3-acetamido-3,6-dideoxy-α-D-glucose
dTDP-D-Qui3NAc
dTDP-Qui3NAc
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](O)[C@H](NC(=O)C)[C@@H](O)2))(=O)[O-])O3))=O)
InChIInChI=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
InChIKeyInChIKey=CWQDRZJUANNJKC-NMSPNFBVSA-L

dTDP-Qui3NAc (dTDP-3-acetamido-3,6-dideoxy-D-glucose) is a nucleotide sugar derivative involved in bacterial glycosylation processes. It plays a key role in the synthesis of complex glycans, specifically in the biosynthesis of polysaccharides in bacterial systems.

Structure & Properties:

  • Molecular Weight (MW): Approximately 547 g/mol
  • Chemical Formula: C17H28N3O14P2S
  • Synonyms: dTDP-3-acetamido-3,6-dideoxy-D-glucose, dTDP-Qui3NAc, dTDP-3-amino-3,6-dideoxy-D-glucose
  • Functional Groups: Contains an acetamido group at the 3-position, a dideoxy modification at the 6-position, and a thymidine diphosphate moiety.

Biological Role:

  • Biosynthesis Pathway: dTDP-Qui3NAc is synthesized from dTDP-3-amino-3,6-dideoxy-D-glucose via acetylation at the 3-position. It serves as an activated donor in bacterial polysaccharide biosynthesis.
  • Function: This sugar nucleotide is utilized in glycan assembly, contributing to the formation of bacterial surface polysaccharides such as O-antigens, capsules, and exopolysaccharides.

Applications:

  1. Bacterial Glycobiology: dTDP-Qui3NAc is an essential component in the biosynthesis of bacterial glycans, particularly those involved in virulence factors like lipopolysaccharides (LPS).
  2. Enzyme Studies: Researchers study the enzymes involved in dTDP-Qui3NAc synthesis and transfer, which are crucial for understanding bacterial cell wall biosynthesis.

Significance in Research:

  1. Pathogen Recognition: dTDP-Qui3NAc is part of the polysaccharides that pathogens use to interact with host immune cells, making it a significant molecule in pathogen-host interactions.
  2. Structural Diversity of Glycans: Its incorporation into bacterial glycans adds to the structural diversity of bacterial cell surfaces, which can influence immune evasion and bacterial survival.

Key Roles:

  • Polysaccharide Biosynthesis: dTDP-Qui3NAc is incorporated into polysaccharides via glycosyltransferases, aiding in the assembly of complex bacterial glycans.
  • Virulence Factor: The sugars produced from dTDP-Qui3NAc are involved in creating structures that help bacteria evade the host immune system and adhere to host tissues.

Storage and Stability:

  • Storage: Store at -20°C in a dry, sealed container to prevent moisture absorption and degradation.
  • Stability: Stable under proper storage conditions but should be kept dry and protected from light to maintain its integrity.

Research Applications:

  1. Antimicrobial Research: Enzymes involved in the synthesis of dTDP-Qui3NAc are potential targets for developing new antibiotics, particularly those that disrupt bacterial polysaccharide biosynthesis.
  2. Vaccine Development: Understanding the role of dTDP-Qui3NAc in polysaccharide biosynthesis can aid in designing vaccines targeting encapsulated bacteria.

Potential Impact:

  • Antibiotic Development: Inhibiting the biosynthesis or utilization of dTDP-Qui3NAc can impair the formation of key bacterial structures, reducing their ability to cause disease.
  • Immune System Evasion: By altering the synthesis of dTDP-Qui3NAc-containing polysaccharides, researchers may develop strategies to reduce bacterial evasion of the immune system.

dTDP-Qui3NAc is a critical molecule in bacterial glycosylation, involved in the formation of polysaccharides that contribute to the virulence and survival of bacterial pathogens. Its role in glycan biosynthesis makes it a target of interest in the development of therapeutic strategies against bacterial infections

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Size

15 MG, 25 MG, 5 MG

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