Diphthamide
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| Names | |
|---|---|
| IUPAC name
2-Amino-3-[2-(3-carbamoyl-3-trimethylammonio-propyl)-3H-imidazol-4-yl]propanoate | |
| Identifiers | |
75645-22-6  | |
| 3D model (Jmol) | Interactive image Interactive image |
| ChemSpider | 4942856 |
| PubChem | 6438375 |
| |
| |
| 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). | |
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| Infobox references | |
Diphthamide is a post-translationally modified histidine amino acid found in archaeal and eukaryotic elongation factor 2 (eEF-2).
Structure
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]
Biological function
Diphthamide ensures translation fidelity.[2]
The presence or absence of diphthamide is known to affect NF-κB or death receptor pathways.[3]
Biosynthesis
Diphthamide is biosynthesized from histidine and S-adenosyl methionine.[2]
References
- ↑ Jorgensen, R (2006). "The life and death of translation elongation factor 2.". Biochem Soc Trans. 34: 1–6. doi:10.1042/BST20060001. PMID 16246167.
- 1 2 Su, Xiaoyang; Lin, Zhewang; Lin, Hening (2013-11-01). "The biosynthesis and biological function of diphthamide". Critical Reviews in Biochemistry and Molecular Biology. 48 (6): 515–521. doi:10.3109/10409238.2013.831023. ISSN 1040-9238. PMC 4280834
. PMID 23971743. - ↑ Stahl, Sebastian (2015). "Loss of diphthamide pre-activates NF-κB and death receptor pathways and renders MCF7 cells hypersensitive to tumor necrosis factor". Proc Natl Acad Sci U S A. 112: 10732–7. doi:10.1073/pnas.1512863112. PMC 4553792. PMID 26261303.
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