![]() | |
Names | |
---|---|
IUPAC name
2-Amino-3-[2-(3-carbamoyl-3-trimethylammonio-propyl)-3H-imidazol-4-yl]propanoate
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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]
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]
In eukaryotes, this biosynthetic pathway contains a total of 7 genes (Dph1-7). [1]
Diphthamide ensures translation fidelity. [1]
The presence or absence of diphthamide is known to affect NF-κB or death receptor pathways. [4]
![]() | |
Names | |
---|---|
IUPAC name
2-Amino-3-[2-(3-carbamoyl-3-trimethylammonio-propyl)-3H-imidazol-4-yl]propanoate
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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]
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]
In eukaryotes, this biosynthetic pathway contains a total of 7 genes (Dph1-7). [1]
Diphthamide ensures translation fidelity. [1]
The presence or absence of diphthamide is known to affect NF-κB or death receptor pathways. [4]