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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.

Structure of base pair Adenine Dihydrouracil (AD)

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

^ Dalluge JJ; Hashizume T; Sopchik AE; McCloskey JA; Davis DR. (Mar 15, 1996). "Conformational flexibility in RNA: the role of dihydrouridine". Nucleic Acids Res 24 (6): 1073–1079. doi:10.1093/nar/24.6.1073. PMC 145759. PMID 8604341.
^ Dalluge JJ; Hamamoto T; Horikoshi K; Morita RY; Stetter KO; McCloskey JA (March 1, 1997). "Posttranscriptional modification of tRNA in psychrophilic bacteria". J Bacteriol 179 (6): 1918–1923. PMC 178914. PMID 9068636.

English Journal

Complete mitochondrial genome of the sixbar grouper Epinephelus sexfasciatus (Perciformes: Epinephelidae).

Du FY1, Ye L, Wang XH.
Mitochondrial DNA.Mitochondrial DNA.2015 Jun;26(3):461-2. doi: 10.3109/19401736.2013.823175. Epub 2013 Sep 11.
In this study, we presented the complete mitogenome for the sixbar grouper Epinephelus sexfasciatus. The complete mitogenome of E. sexfasciatus is 16,786 bp in length with the typical mitochondrial gene order and composition in vertebrates. Overall base composition was 28.40% A, 27.93% C, 27.21% T
PMID 24021001

The complete mitochondrial genome of Bryodema miramae (Orthoptera: Oedipodidae).

Hao J1, Liu N, Zhou F, Huang Y.
Mitochondrial DNA.Mitochondrial DNA.2015 May 29:1-2. [Epub ahead of print]
The complete circular mitochondrial genome (mitogenome) of Bryodema miramae is 15,919 bp in length, containing 37 typical genes and 1 non-coding AT-rich region. The AT content of the AT-rich region is 84.7%. All protein-coding genes (PCGs) start with standard ATN initiation codon and end with comple
PMID 26024137

The complete mitochondrial genome of the butterfly Euripus nyctelius (Lepidoptera: Nymphalidae).

Xuan S1, Song F, Cao L, Wang J, Li H, Cao T.
Mitochondrial DNA.Mitochondrial DNA.2015 May 29:1-3. [Epub ahead of print]
The complete mitochondrial genome (mitogenome) of the butterfly, Euripus nyctelius, was determined in the present study. The mitogenome is a typical circular DNA molecule of 15,417 bp, containing 37 genes and a putative control region. Thirteen protein-coding genes all initiate with ATN codons and
PMID 26024135

Japanese Journal

In vitro dihydrouridine formation by tRNA dihydrouridine synthase from Thermus thermophilus, an extreme-thermophilic eubacterium

The journal of biochemistry 158(6), 513-521, 2015-12
NAID 40020683886

tRNAジヒドロウリジン合成酵素の分子機構

生化学 86(3), 395-399, 2014-06
NAID 40020153827

Structure of dihydrouridine synthase C (DusC) from Escherichia coli

Acta Crystallographica Section F : Structural Biology And Crystallization Communications 69(8), 834-838, 2013-08
NAID 120005317013

Related Pictures

STRUCTURE DES ACIDES NUCLEIQUES - ppt video online télécharger Human Dihydrouridine Synthase 3-Like (S. Cerevisiae) (DUS3L) Protein (GST tag tRNA Trna-Dihydrouridine Synthase by Aloysius, Dewayne Rocky [Paperback] | Jet.com tRNA-dihydrouridine synthase - Wikipedia Protein Synthesis -Translation and Regulation Molecular evolution of dihydrouridine synthases | BMC Bioinformatics | Full Text Human Dihydrouridine Synthase 1-Like (S. Cerevisiae) (DUS1L) Protein (GST tag

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リンク元	「ジヒドロウリジン」
拡張検索	「dihydrouridine arm」

「ジヒドロウリジン」

Dihydrouridine
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
CAS Registry Number	5627-05-4
ChemSpider	85115
	InChI 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 ; Key: ZPTBLXKRQACLCR-XVFCMESISA-N ; 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 ;
Jmol-3D images	Image; Image
PubChem	94312
	SMILES 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
Chemical formula	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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英: dihydrouridine
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[1] Dalluge JJ; Hashizume T; Sopchik AE; McCloskey JA; Davis DR. (Mar 15, 1996). "Conformational flexibility in RNA: the role of dihydrouridine". Nucleic Acids Res 24 (6): 1073–1079. doi:10.1093/nar/24.6.1073. PMC 145759. PMID 8604341.

[2] Dalluge JJ; Hamamoto T; Horikoshi K; Morita RY; Stetter KO; McCloskey JA (March 1, 1997). "Posttranscriptional modification of tRNA in psychrophilic bacteria". J Bacteriol 179 (6): 1918–1923. PMC 178914. PMID 9068636.

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dihydrouridine