Diphthamide

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Diphthamide
Diphthamide.png
Names
IUPAC name
2-Amino-3-[2-(3-carbamoyl-3-trimethylammonio-propyl)-3H-imidazol-4-yl]propanoate
Identifiers
75645-22-6 YesY
ChemSpider 4942856 YesY
Jmol 3D model Interactive image
Interactive image
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).
YesY verify (what is YesYN ?)
Infobox references

Diphthamide is a post-translationally modified histidine amino acid found in archaeal and eukaryotic elongation factor 2 (eEF-2).

Structure[edit]

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[edit]

Diphthamide ensures translation fidelity.[2]

The presence or absence of diphthamide is known to affect NF-κB or death receptor pathways.[3]

Biosynthesis[edit]

Diphthamide is biosynthesized from histidine and S-adenosyl methionine.[2]

References[edit]

  1. ^ Jorgensen, R (2006). "The life and death of translation elongation factor 2.". Biochem Soc Trans. 34: 1–6. doi:10.1042/BST20060001. PMID 16246167. 
  2. ^ a b 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 4280834free to read. PMID 23971743. 
  3. ^ 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 4553792free to read. PMID 26261303.