Dihydrouridine
170px | |
Names | |
---|---|
IUPAC name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-diazinane-2,4-dione
|
|
Other names
3,4-dihydrouridine
3,4,5,6-tetrahydrouridine 5,6-dihydrouridine |
|
Identifiers | |
5627-05-4 ![]() |
|
ChemSpider | 85115 ![]() |
Jmol 3D model | Interactive image Interactive image |
PubChem | 94312 |
|
|
|
|
Properties | |
C9H14N2O6 | |
Molar mass | 246.217 g/mol |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|
![]() ![]() ![]() |
|
Infobox references | |
Dihydrouridine (abbreviated as D, DHU, or UH2) is a pyrimidine which is the result of adding two hydrogen atoms to a uridine, making it a fully saturated pyrimidine ring with no remaining double bonds. D is found in tRNA and rRNA molecules as a nucleoside; the corresponding nucleobase is 5,6-dihydrouracil.
Because it is non-planar, D disturbs the stacking interactions in helices and destabilizes the RNA structure. D also stabilizes the C2’-endo sugar conformation, which is more flexible than the C3’-endo conformation, and this effect is propagated to the 5’-neighboring residue. Thus, while pseudouridine and 2’-O-methylations stabilize the local RNA structure, D does the opposite.[1]
tRNA of organisms that grow at low temperatures (psychrophiles) have high 5,6-dihydrouridine levels (40-70% more on average) which provides the necessary, local, flexibility of the tRNA at or below the freezing point.[2]
References
- Pages with broken file links
- Articles without EBI source
- Articles without KEGG source
- Articles without UNII source
- Articles with changed InChI identifier
- Pages using collapsible list with both background and text-align in titlestyle
- Chemical articles using a fixed chemical formula
- Nucleosides
- Pyrimidinediones