Chemistry:Diphthamide
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| IUPAC name
2-Amino-3-[2-(3-carbamoyl-3-trimethylammonio-propyl)-3H-imidazol-4-yl]propanoate
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| 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). | |
 verify (what is   ?)
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| Infobox references | |
Tracking categories (test):
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 (Pt 1): 1–6. doi:10.1042/BST20060001. PMID 16246167.
- ↑ 2.0 2.1 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. 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 (34): 10732–7. doi:10.1073/pnas.1512863112. PMID 26261303. Bibcode: 2015PNAS..11210732S.
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