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Dihydrouridine

Chemical compound From Wikipedia, the free encyclopedia

Dihydrouridine (abbreviated as D,[1]: N3.2.1  hU,[1]: N4.1  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.

Structure of base pair Adenine Dihydrouracil (AD)
Quick facts Names, Identifiers ...
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)
ChemSpider
ECHA InfoCard 100.257.727 Edit this at Wikidata
UNII
  • InChI=1S/C9H14N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h4,6-8,12,14-15H,1-3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1 X markN
    Key: ZPTBLXKRQACLCR-XVFCMESISA-N X markN
  • InChI=1/C9H14N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h4,6-8,12,14-15H,1-3H2,(H,10,13,16)/t4-,6-,7-,8-/m1/s1
    Key: ZPTBLXKRQACLCR-XVFCMESIBI
  • C1CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
  • O=C1N(CCC(=O)N1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
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).
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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.[2]

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.[3]

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