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
CAS Number	94102-64-4; 118013-66-4 deprecated;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:46763;
ChemSpider	143523;
DrugBank	DB04736;
PubChem CID	163626;
UNII	MJ92ND3XT9;
CompTox Dashboard (EPA)	DTXSID90276530 ;
	InChI InChI=1S/C37H59N7O20/c1-13(30(51)44-20(35(58)59)9-10-23(48)43-19(8-6-7-18(38)34(56)57)32(53)40-14(2)33(54)55)39-31(52)15(3)61-29-25(42-17(5)47)36-60-12-22(63-36)28(29)64-37-24(41-16(4)46)27(50)26(49)21(11-45)62-37/h13-15,18-22,24-29,36-37,45,49-50H,6-12,38H2,1-5H3,(H,39,52)(H,40,53)(H,41,46)(H,42,47)(H,43,48)(H,44,51)(H,54,55)(H,56,57)(H,58,59)/t13-,14+,15+,18+,19-,20+,21+,22+,24+,25+,26+,27+,28+,29+,36+,37-/m0/s1 Key: UPFMKPIBAIPLHT-RSJSDIDPSA-N;
	SMILES 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
Chemical formula	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.