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diphthamide
Sign in to saveAlso known as (2S)-2-amino-3-[2-[(3S)-4-amino-4-oxo-3-(trimethylazaniumyl)butyl]-1H-imidazol-5-yl]propanoate
Diphthamide is a post-translationally modified histidine amino acid found in archaeal and eukaryotic elongation factor 2 (eEF-2).
Chemical data
- Formula
- C13H24N5O3+
- Molecular weight
- 298.36 g/mol
- IUPAC name
- [(2S)-1-amino-4-[5-[(2S)-2-amino-2-carboxyethyl]-1H-imidazol-2-yl]-1-oxobutan-2-yl]-trimethylazanium
- SMILES
- C[N+](C)(C)[C@@H](CCC1=NC=C(N1)C[C@@H](C(=O)O)N)C(=O)N
- InChIKey
- FOOBQHKMWYGHCE-UWVGGRQHSA-O
- XLogP
- -3.5
- Polar surface area
- 135 Ų
- H-bond donors
- 4
- H-bond acceptors
- 5
- Formal charge
- 1
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 298.18736604809
Show 3 more facts
- canonical SMILES
- C[N+](C)(C)C(CCC1=NC=C(N1)CC(C(=O)O)N)C(=O)N
- isomeric SMILES
- C[N+](C)(C)[C@@H](CCC1=NC=C(N1)C[C@@H](C(=O)O)N)C(=O)N
- chemical formula
- C₁₃H₂₄N₅O₃⁺
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Structure and biosynthesis
- Biological function
- References
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. Besides this toxin, it is also targeted by exotoxin A from Pseudomonas aeruginosa. It is the only target of these toxins.
Excerpted from Wikipedia’s “diphthamide” article, available under the CC BY-SA 4.0 licence.