Dihydrouridine
| Names | |
|---|---|
| IUPAC name
5,6-Dihydrouridine | |
| Systematic IUPAC name
1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-diazinane-2,4-dione | |
| Other names
1,3,5,6-tetrahydrouridine | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.257.727 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C9H14N2O6 | |
| Molar mass | 246.217 g/mol |
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 nucleoside 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; 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.
The tRNAs 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.