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queuine
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Queuine () (Q) is a hypermodified nucleobase found in the first (or wobble) position of the anticodon of tRNAs specific for Asn, Asp, His, and Tyr, in most eukaryotes and prokaryotes. Because it is utilized by all eukaryotes but produced exclusively by bacteria, it is a putative vitamin.
Chemical data
- Formula
- C12H15N5O3
- Molecular weight
- 277.28 g/mol
- IUPAC name
- 2-amino-5-[[[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino]methyl]-1,7-dihydropyrrolo[2,3-d]pyrimidin-4-one
- SMILES
- C1=C[C@@H]([C@@H]([C@H]1NCC2=CNC3=C2C(=O)N=C(N3)N)O)O
- InChIKey
- WYROLENTHWJFLR-ACLDMZEESA-N
- XLogP
- -2.4
- Polar surface area
- 136 Ų
- H-bond donors
- 6
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 277.117
Show 4 more facts
- found in taxon
- Caenorhabditis elegans
- chemical formula
- C₁₂H₁₅N₅O₃
- canonical SMILES
- C1=CC(C(C1NCC2=CNC3=C2C(=O)N=C(N3)N)O)O
- isomeric SMILES
- C1=C[C@@H]([C@@H]([C@H]1NCC2=CNC3=C2C(=O)N=C(N3)N)O)O
Sources (2)
via Wikidata · CC0
~5 min read
Encyclopedic overview
5 sectionsContents
- History and naming
- Biosynthesis and function
- Enzyme research
- References
- External links
{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 447003644 | ImageFile=Queuine.svg | ImageSize=240px | PIN=2-Amino-5-({[(1S,4S,5R)-4,5-dihydroxycyclopent-2-en-1-yl]amino}methyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one | OtherNames= 7-(((4,5-cis-dihydroxy-2-cyclopenten-1-yl)amino)methyl)-7-deazaguanine |Section1= |Section2= |Section3= }}
Queuine () (Q) is a hypermodified nucleobase found in the first (or wobble) position of the anticodon of tRNAs specific for Asn, Asp, His, and Tyr, in most eukaryotes and prokaryotes. Because it is utilized by all eukaryotes but produced exclusively by bacteria, it is a putative vitamin.
Excerpted from Wikipedia’s “queuine” article, available under the CC BY-SA 4.0 licence.