Tracheal cytotoxin

Tat-BP
Names
IUPAC name
(2R,6S)-6-[[(4R)-4-[[(2S)-2-[[(2R)-2-[[(1R,2S,3R,4R,5R)-4-acetamido-2-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy]propanoyl]amino]propanoyl]amino]-4-carboxybutanoyl]amino]-2-amino-7-[[(1R)-1-carboxyethyl]amino]-7-oxoheptanoic acid
Other names
  • TCT
  • Tracheal cytotoxin, bordetella pertussis
  • GlcNAc(beta1-4)-MurNAc(1,6-anhydro)-L-Ala-gamma-D-Glu-meso-A2pm-D-Ala
  • GlcNAc-1,6-anhMurNAc-L-Ala-gamma-D-Glu-DAP-D-Ala (physiological form; two fewer protons)
Identifiers
3D model (JSmol)
DrugBank
  • C[C@@H](C(=O)N[C@H](CCC(=O)N[C@@H](CCC[C@H](C(=O)O)N)C(=O)N[C@H](C)C(=O)O)C(=O)O)NC(=O)[C@@H](C)O[C@@H]1[C@H]([C@@H]2OC[C@H]([C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)NC(=O)C)O2)NC(=O)C
Properties
C37H59N7O20
Molar mass 921.908 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tracheal cytotoxin (TCT) is a 921 dalton glycopeptide released by Bordetella pertussis, Vibrio fischeri (as a symbiosis chemical), and Neisseria gonorrhoeae (among other peptidoglycan-derived cytotoxins it produces). It is a soluble piece of peptidoglycan (PGN) found in the cell wall of all gram-negative bacteria, but only some bacteria species release TCT due to inability to recycle this piece of anhydromuropeptide.

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