Diphthamide

Diphthamide
Names
IUPAC name
2-Amino-3-[2-(3-carbamoyl-3-trimethylammonio-propyl)-3H-imidazol-4-yl]propanoate
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C13H23N5O3/c1-18(2,3)10(12(15)19)4-5-11-16-7-8(17-11)6-9(14)13(20)21/h7,9-10H,4-6,14H2,1-3H3,(H3-,15,16,17,19,20,21) checkY
    Key: FOOBQHKMWYGHCE-UHFFFAOYSA-N checkY
  • InChI=1/C13H23N5O3/c1-18(2,3)10(12(15)19)4-5-11-16-7-8(17-11)6-9(14)13(20)21/h7,9-10H,4-6,14H2,1-3H3,(H3-,15,16,17,19,20,21)
    Key: FOOBQHKMWYGHCE-UHFFFAOYAN
  • C[N+](C)(C)C(CCC1=NC=C(N1)CC(C(=O)[O-])N)C(=O)N
  • [O-]C(=O)C(N)Cc1cnc([nH]1)CCC(C(=O)N)[N+](C)(C)C
Properties
C13H23N5O3
Molar mass 297.354 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Diphthamide is a post-translationally modified histidine amino acid found in archaeal and eukaryotic elongation factor 2 (eEF-2).

Dipthamide is named after the toxin produced by the bacterium Corynebacterium diphtheriae, which targets diphthamide.[1] Besides this toxin, it is also targeted by exotoxin A from Pseudomonas aeruginosa.[1][2] It is the only target of these toxins.[2]

  1. ^ a b Cite error: The named reference pmc4280834 was invoked but never defined (see the help page).
  2. ^ a b Liu S, Wiggins JF, Sreenath T, Kulkarni AB, Ward JM, Leppla SH (May 2006). "Dph3, a small protein required for diphthamide biosynthesis, is essential in mouse development". Molecular and Cellular Biology. 26 (10): 3835–3841. doi:10.1128/MCB.26.10.3835-3841.2006. PMC 1488998. PMID 16648478.