| Revision as of 18:27, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443355526 of page 5-Bromouracil for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 21:47, 11 December 2021 edit DePiep (talk | contribs)Extended confirmed users294,285 editsm →top: GHS update: remove empty EUClass/Rphrase/Sphrase parameters (depr), replaced: | EUClass = | → | (3), | SPhrases = | → |Tag: AWB |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443354280 |
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| verifiedrevid = 477224151 |
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| ImageFile = 5-Bromouracil structure.png |
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| ImageFile = 5-Bromouracil structure.png |
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| ImageSize = 150px |
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| ImageSize = 150px |
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| IUPACName = 5-Bromo-1H-pyrimidine-2,4-dione |
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| PIN = 5-Bromopyrimidine-2,4(1''H'',3''H'')-dione |
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| OtherNames = 5-Bromo-2,4-dihydroxypyrimidine |
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| OtherNames = 5-Bromo-2,4-dihydroxypyrimidine<br />5-Bromopyrimidine-2,4-dione |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = 5-BrU<br>5-BU |
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| Abbreviations = 5-BrU<br />br5Ura<br />5BrUra |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5597 |
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| ChemSpiderID = 5597 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 51-20-7 |
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| CASNo = 51-20-7 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 4HK400G5UO |
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| EINECS = |
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| EINECS = |
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| PubChem = 5802 |
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| PubChem = 5802 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = |
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}} |
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| ATCCode_prefix = |
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⚫ |
|Section2={{Chembox Properties |
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| ATCCode_suffix = |
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| C=4|H=3|Br=1|N=2|O=2 |
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| ATC_Supplemental =}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>4</sub>H<sub>3</sub>BrN<sub>2</sub>O<sub>2</sub> |
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| MolarMass = 190.983 g/mol |
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| pKa = |
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| pKa = |
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| pKb = }} |
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| pKb = }} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| EUClass = |
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| EUIndex = |
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| MainHazards = |
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| PEL = }} |
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}} |
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}} |
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'''5-Bromouracil''' ('''5-BrU''', '''5BrUra''', or '''br5Ura'''<ref>{{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 = ] | volume = 9 | issue = 20 | pages = 4022–4027 | year = 1970 }}</ref>) is a brominated derivative of ] that acts as an ] or ], substituting for ] in ], and can induce DNA ] in the same way as ].<ref>{{cite book|last1=Griffiths|first1=Anthony J.F.|last2=Wessler | first2=Susan R. |last3=Carroll | first3=Sean B. | last4=Doebley | first4=John | title=Introduction to Genetic Analysis|date=2012|publisher=W.H. Freeman and Company|location=New York|isbn=978-1-4292-2943-2|edition=10th}}</ref> It is used mainly as an experimental ], but its deoxyriboside derivative (]) is used to treat ]s. |
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5-BrU exists in three ]ic forms that have different base pairing properties. The ] form (shown in the infobox) is complementary to ], so it can be incorporated into DNA by aligning opposite adenine residues during DNA replication (see below left). Alternatively, the ] (below right) and ion forms are complementary to ]. This means that 5-BrU can be present in DNA either opposite adenine or guanine. |
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] |
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The three forms frequently interchange so base-pairing properties can become altered at any time. The result of this is that during a subsequent round of replication a different base is aligned opposite the 5-BrU residue. Further rounds of replication 'fix' the change by incorporating a normal nitrogen base into the complementary strand. |
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]{{clear-left}} |
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Thus 5-BrU induces a ] via base substitution. This base pair will change from an A-T to a G-C or from a G-C to an A-T after a number of replication cycles, depending on whether 5-BrU is within the DNA molecule or is an incoming base when it is enolized or ionized. |
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== See also == |
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* ] |
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* ] |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Bromouracil, 5-}} |
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] |
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] |
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] |
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] |