“Dihydrouridine”的意思、由来-开放百科全书

词条

Dihydrouridine

释义

References

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 433119591
| ImageFile = Dihydrouridine.svg
| ImageSize = 170px
| IUPACName = 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-diazinane-2,4-dione
| OtherNames = 5,6-dihydrouridine
1,3,5,6-tetrahydrouridine

|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 5627-05-4
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 0D5FR359JO
| EINECS =
| PubChem = 94312
| SMILES = C1CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 85115
| SMILES2 = O=C1N(CCC(=O)N1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
| 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
| InChIKey = ZPTBLXKRQACLCR-XVFCMESIBI
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = ZPTBLXKRQACLCR-XVFCMESISA-N
|Section2={{Chembox Properties
| Formula = C₉H₁₄N₂O₆
| MolarMass = 246.217 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

Dihydrouridine (abbreviated as D^[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.

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.^[2]

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.^[3]

References

1. ^{{Cite journal | author = IUPAC-IUB Commission on Biochemical Nomenclature | doi = 10.1021/bi00822a023 | title = Abbreviations and symbols for nucleic acids, polynucleotides, and their constituents | journal = Biochemistry | volume = 9 | issue = 20 | pages = 4022–4027 | year = 1970 | pmid = 5499957 | pmc = 1179624}}
2. ^ {{cite journal| title=Conformational flexibility in RNA: the role of dihydrouridine| date=Mar 15, 1996| pmid=8604341| author=Dalluge JJ|author2=Hashizume T |author3=Sopchik AE |author4=McCloskey JA |author5=Davis DR. | journal=Nucleic Acids Res| volume=24| pages=1073–1079| doi=10.1093/nar/24.6.1073| issue=6| pmc=145759}}
3. ^ {{cite journal| title=Posttranscriptional modification of tRNA in psychrophilic bacteria| date= March 1, 1997 | pmid=9068636| author=Dalluge JJ |author2=Hamamoto T |author3=Horikoshi K |author4=Morita RY |author5=Stetter KO |author6=McCloskey JA | journal=J Bacteriol| volume=179| pages=1918–1923| issue=6| pmc=178914}}

2 : Nucleosides|Pyrimidinediones

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