Modification of DNA with octadiynyl side chains: Synthesis, base pairing, and formation of fluorescent coumarin dye conjugates of four nucleobases by the alkyne-azide ``click'' reaction
DC Element | Wert | Sprache |
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dc.contributor.author | Seela, Frank | |
dc.contributor.author | Sirivolu, Venkata Ramana | |
dc.contributor.author | Chittepu, Padmaja | |
dc.date.accessioned | 2021-12-23T16:05:35Z | - |
dc.date.available | 2021-12-23T16:05:35Z | - |
dc.date.issued | 2008 | |
dc.identifier.issn | 10431802 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/7086 | - |
dc.description.abstract | Oligonucleotides incorporating 5-(octa-1,7-diynyl)-2'-deoxycytidine 1a, 5-(octa-1,7-diynyl)-2'-deoxyuridine 2a and 7-deaza-7-(octa-1,7-diynyl)-2'-deoxyguanosine 3a, 7-deaza-7-(octa-1,7-diynyl)-2'-deoxyadenosine 4a were prepared. For this, the phosphoramidites 7, 10, and 13 were synthesized and employed in solid-phase oligonucleotide synthesis. The octa-1,7-diynyl nucleosides 1a-4a were obtained from their corresponding iodo derivatives using the palladium-assisted Sonogashira cross-coupling reaction. The Tm values demonstrated that DNA duplexes containing octa-1,7-diynyl nucleosides show a positive influence on the DNA duplex stability when they are introduced at the 5-position of pyrimidines or at the 7-position of 7-deazapurines. The terminal alkyne residue of oligonucleotides were selectively conjugated to the azide residue of the nonfluorescent 3-azido-7-hydroxycoumarin (38) using the protocol of copper(I)-catalyzed [3 2] Huisgen-Sharpless-Meldal cycloaddition ``click chemistry'' resulting in the formation of strongly fluorescent 1,2,3-triazole conjugates. The fluorescence properties of oligonucleotides with covalently linked coumarin-nucleobase assemblies were investigated. Among the four modified bases, the 7-deazapurines show stronger fluorescence quenching than that of pyrimidines. | |
dc.language.iso | en | |
dc.publisher | AMER CHEMICAL SOC | |
dc.relation.ispartof | BIOCONJUGATE CHEMISTRY | |
dc.subject | 2-DEOXYURIDINE | |
dc.subject | ANTISENSE GENE INHIBITION | |
dc.subject | Biochemical Research Methods | |
dc.subject | Biochemistry & Molecular Biology | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | Chemistry, Organic | |
dc.subject | DERIVATIVES | |
dc.subject | DUPLEXES | |
dc.subject | FUNCTIONALIZATION | |
dc.subject | OLIGODEOXYNUCLEOTIDES | |
dc.subject | OLIGONUCLEOTIDES | |
dc.subject | PROPYNE ANALOGS | |
dc.subject | PYRIMIDINES | |
dc.subject | STABILITY | |
dc.title | Modification of DNA with octadiynyl side chains: Synthesis, base pairing, and formation of fluorescent coumarin dye conjugates of four nucleobases by the alkyne-azide ``click'' reaction | |
dc.type | journal article | |
dc.identifier.doi | 10.1021/bc700300f | |
dc.identifier.isi | ISI:000252520300028 | |
dc.description.volume | 19 | |
dc.description.issue | 1 | |
dc.description.startpage | 211 | |
dc.description.endpage | 224 | |
dc.identifier.eissn | 15204812 | |
dc.publisher.place | 1155 16TH ST, NW, WASHINGTON, DC 20036 USA | |
dcterms.isPartOf.abbreviation | Bioconjugate Chem. |
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geprüft am 01.06.2024