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| Names | |
|---|---|
| IUPAC name 2-Amino-3-[2-(3-carbamoyl-3-trimethylammonio-propyl)-3H-imidazol-4-yl]propanoate | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider |
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| UNII | |
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| Properties | |
| C13H23N5O3 | |
| Molar mass | 297.354 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Diphthamide is a post-translationally modifiedhistidineamino acid found in archaeal andeukaryotic elongation factor 2 (eEF-2).
Dipthamide is named after the toxin produced by the bacteriumCorynebacterium diphtheriae, which targets diphthamide.[1] Besides this toxin, it is also targeted byexotoxin A fromPseudomonas aeruginosa.[1][2] It is the only target of these toxins.[2]
Diphthamide is proposed to be a 2-[3-carboxyamido-3-(trimethylammonio)propyl]histidine. Though this structure has been confirmed byX-ray crystallography, its stereochemistry is uncertain.[1][3]
Diphthamide is biosynthesized from histidine andS-adenosyl methionine (SAM).[1] The side chain bound toimidazole group and allmethyl groups come from SAM. The whole synthesis takes place in three steps:[1]
In eukaryotes, this biosynthetic pathway contains a total of 7 genes (Dph1-7).[1]
Diphthamide ensurestranslation fidelity.[1]
The presence or absence of diphthamide is known to affectNF-κB ordeath receptor pathways.[4]
