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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).

Tracheal cytotoxin (TCT) is a 921 dalton glycopeptide released by Bordetella pertussis,[1] Vibrio fischeri (as a symbiosis chemical),[2] and Neisseria gonorrhoeae (among other peptidoglycan-derived cytotoxins it produces).[3] It is a soluble piece of peptidoglycan (PGN) found in the cell wall of all gram-negative bacteria,[4] but only some bacteria species release TCT due to inability to recycle this piece of anhydromuropeptide.[5]

  1. ^ Cundell, DR; Kanthakumar, K; Taylor, GW; Goldman, WE; Flak, T; Cole, PJ; Wilson, R (1994). "Effect of tracheal cytotoxin from Bordetella pertussis on human neutrophil function in vitro". Infection and Immunity. 62 (2): 639–43. doi:10.1128/iai.62.2.639-643.1994. PMC 186151. PMID 8300220.
  2. ^ Koropatnick, TA; Engle, JT; Apicella, MA; Stabb, EV; Goldman, WE; McFall-Ngai, MJ (12 November 2004). "Microbial factor-mediated development in a host-bacterial mutualism". Science. 306 (5699): 1186–8. Bibcode:2004Sci...306.1186K. doi:10.1126/science.1102218. PMID 15539604. S2CID 41603462. Here, we report that Vibrio fischeri also releases TCT, which acts in synergy with lipopolysaccharide (LPS) to trigger tissue development in its mutualistic symbiosis with the squid Euprymna scolopes.
  3. ^ Cloud, KA; Dillard, JP (June 2002). "A lytic transglycosylase of Neisseria gonorrhoeae is involved in peptidoglycan-derived cytotoxin production". Infection and Immunity. 70 (6): 2752–7. doi:10.1128/IAI.70.6.2752-2757.2002. PMC 127960. PMID 12010959. A major peptidoglycan fragment released by gonococci is identical to the tracheal cytotoxin of Bordetella pertussis and has been shown to kill ciliated fallopian tube cells in organ culture.
  4. ^ Mattoo, S.; Cherry, J. D. (2005). "Molecular Pathogenesis, Epidemiology, and Clinical Manifestations of Respiratory Infections Due to Bordetella pertussis and Other Bordetella Subspecies". Clinical Microbiology Reviews. 18 (2): 326–82. doi:10.1128/CMR.18.2.326-382.2005. PMC 1082800. PMID 15831828.
  5. ^ Cite error: The named reference Parkhill03 was invoked but never defined (see the help page).
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