Pyrrolo-dC oligonucleotides bearing alkynyl side chains with terminal triple bonds: synthesis, base pairing and fluorescent dye conjugates prepared by the azide-alkyne ``click'' reaction
DC Element | Wert | Sprache |
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dc.contributor.author | Seela, Frank | |
dc.contributor.author | Sirivolu, Venkata Ramana | |
dc.date.accessioned | 2021-12-23T16:12:09Z | - |
dc.date.available | 2021-12-23T16:12:09Z | - |
dc.date.issued | 2008 | |
dc.identifier.issn | 14770520 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/10068 | - |
dc.description.abstract | 5-(Octa-1,7-diynyl)-2'-deoxyuridine was converted into the furano-dU derivative 7 by copper-catalyzed cyclization; the pyrolodC-derivative 3 was formed upon ammonolysis. The bicyclic nucleosides 3 and 7 as well as the corresponding non-cyclic precursors 4 and 6 all containing terminal C C bonds were conjugated with the non-fluorescent 3-azido-7-hydroxycoumarin 5 employing the copper(I)-catalyzed Huisgen-Sharpless-Meldal cycloaddition ``click reaction''. Strongly fluorescent 1H-1,2,3-triazole conjugates (30-33) are formed incorporating two fluorescent reporters-the pyrdC nucleoside and the coumarin moiety. Oligonucleotides incorporating 6-alkynyl and 6-alkyl 7H-pyrrolo[2,3-d] pyrimidin-2(3H)-one nucleosides (3 and 2f) have been prepared by solid-phase synthesis using the phosphoramidite building blocks 10 and 13; the pyrrolo-dC oligonucleotides are formed during ammonia treatment. The duplex stability of oligonucleotides containing 3 and related derivatives was studied. Oligonucleotides with terminal triple bonded nucleosides such as 3 are more stabilizing than those lacking a side chain with terminal unsaturation; open-chain derivatives (4) are even more efficient. The click reaction was also performed on oligonucleotides containing the pyrdC-derivative 3 and the fluorescence properties of nucleosides, oligonucleotides and their coumarin conjugates were studied. | |
dc.language.iso | en | |
dc.publisher | ROYAL SOC CHEMISTRY | |
dc.relation.ispartof | ORGANIC & BIOMOLECULAR CHEMISTRY | |
dc.subject | 1,3-DIPOLAR CYCLOADDITION REACTION | |
dc.subject | 2'-DEOXYCYTIDINE | |
dc.subject | 3,N-4-ETHENO | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Organic | |
dc.subject | COUMARIN | |
dc.subject | DNA | |
dc.subject | FUNCTIONALIZATION | |
dc.subject | NUCLEOSIDE ANALOGS | |
dc.subject | PROBE | |
dc.subject | ZOSTER-VIRUS VZV | |
dc.title | Pyrrolo-dC oligonucleotides bearing alkynyl side chains with terminal triple bonds: synthesis, base pairing and fluorescent dye conjugates prepared by the azide-alkyne ``click'' reaction | |
dc.type | journal article | |
dc.identifier.doi | 10.1039/b719459e | |
dc.identifier.isi | ISI:000255062300022 | |
dc.description.volume | 6 | |
dc.description.issue | 9 | |
dc.description.startpage | 1674 | |
dc.description.endpage | 1687 | |
dc.identifier.eissn | 14770539 | |
dc.publisher.place | THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND | |
dcterms.isPartOf.abbreviation | Org. Biomol. Chem. |
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geprüft am 04.06.2024