Diphthamide

Diphthamide
Names
	IUPAC name 2-Amino-3-[2-(3-carbamoyl-3-trimethylammonio-propyl)-3H-imidazol-4-yl]propanoate
Identifiers
CAS Number	75645-22-6 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	4942856 ;
PubChem CID	6438375;
CompTox Dashboard (EPA)	DTXSID60904010 ;
	InChI InChI=1S/C13H23N5O3/c1-18(2,3)10(12(15)19)4-5-11-16-7-8(17-11)6-9(14)13(20)21/h7,9-10H,4-6,14H2,1-3H3,(H3-,15,16,17,19,20,21) Key: FOOBQHKMWYGHCE-UHFFFAOYSA-N ; InChI=1/C13H23N5O3/c1-18(2,3)10(12(15)19)4-5-11-16-7-8(17-11)6-9(14)13(20)21/h7,9-10H,4-6,14H2,1-3H3,(H3-,15,16,17,19,20,21) Key: FOOBQHKMWYGHCE-UHFFFAOYAN;
	SMILES C[N+](C)(C)C(CCC1=NC=C(N1)CC(C(=O)[O-])N)C(=O)N; [O-]C(=O)C(N)Cc1cnc([nH]1)CCC(C(=O)N)[N+](C)(C)C;
Properties
Chemical formula	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 (Pt 1): 1–6. doi:10.1042/BST20060001. PMID 16246167.
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 (34): 10732–7. Bibcode:2015PNAS..11210732S. doi:10.1073/pnas.1512863112. PMC 4553792. PMID 26261303.

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[:0-1] 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.

[pmc4280834-2] 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.

[:1-3] 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 (34): 10732–7. Bibcode:2015PNAS..11210732S. doi:10.1073/pnas.1512863112. PMC 4553792. PMID 26261303.