Structure via PubChem · Public domain (PubChem)
wybutosine
Sign in to saveIn biochemistry, wybutosine (yW) is a heavily modified nucleoside of phenylalanine transfer RNA that stabilizes interactions between the codons and anti-codons during protein synthesis. Ensuring accurate synthesis of protein is essential in maintaining health as defects in tRNA modifications are able to cause disease. In eukaryotic organisms, it is found only in position 37, 3'-adjacent to the anticodon, of phenylalanine tRNA. Wybutosine enables correct translation through the stabilization of the codon-anticodon base pairing during the decoding process.
Chemical data
- Formula
- C21H28N6O9
- Molecular weight
- 508.5 g/mol
- IUPAC name
- methyl (2S)-4-[3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4,6-dimethyl-9-oxoimidazo[1,2-a]purin-7-yl]-2-(methoxycarbonylamino)butanoate
- SMILES
- CC1=C(N2C(=O)C3=C(N(C2=N1)C)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O)CC[C@@H](C(=O)OC)NC(=O)OC
- InChIKey
- QAOHCFGKCWTBGC-QHOAOGIMSA-N
- XLogP
- -0.5
- Polar surface area
- 191 Ų
- H-bond donors
- 4
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- nucleoside
- Mass
- 508.1917764759998
Show 3 more facts
- isomeric SMILES
- CC1=C(N2C(=O)C3=C(N(C2=N1)C)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O)CC[C@@H](C(=O)OC)NC(=O)OC
- chemical formula
- C₂₁H₂₈N₆O₉
- canonical SMILES
- COC(=O)NC(CCc1c(C)nc2n(C)c3c(ncn3C3OC(CO)C(O)C3O)c(=O)n12)C(=O)OC
Sources (2)
via Wikidata · CC0
~9 min read
Encyclopedic overview
10 sectionsContents
- Biosynthesis
- Variation
- Verification by chemical synthesis
- Function
- Structural effect
- Avoidance of frameshifting
- Alternatives
- Selective allowance of frameshifting?
- Downstream effects
- References
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Excerpted from Wikipedia’s “wybutosine” article, available under the CC BY-SA 4.0 licence.