Diphthamide

Source: Wikipedia, the free encyclopedia.
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

exotoxin A from Pseudomonas aeruginosa.[1][2] It is the only target of these toxins.[2]

Structure and biosynthesis

Diphthamide is proposed to be a 2-[3-carboxyamido-3-(trimethylammonio)propyl]histidine. Though this structure has been confirmed by X-ray crystallography, its stereochemistry is uncertain.[1][3]

Diphthamide is biosynthesized from histidine and S-adenosyl methionine (SAM).[1] The side chain bound to imidazole group and all methyl groups come from SAM. The whole synthesis takes place in three steps:[1]

  • transfer of 3-amino-3-carboxylpropyl group from SAM
  • transfer of three methyl groups from SAM – synthesis of diphtine
  • amidation
    – synthesis of diphthamide

In eukaryotes, this biosynthetic pathway contains a total of 7 genes (Dph1-7).[1]

Biological function

Diphthamide ensures translation fidelity.[1]

The presence or absence of diphthamide is known to affect NF-κB or death receptor pathways.[4]

References

  1. ^
    PMID 23971743
    .
  2. ^
    PMID 16648478
    .
  3. PMID 16246167
    .
  4. PMID 26261303
    .
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