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

Autor(en): Seela, Frank
Sirivolu, Venkata Ramana
Stichwörter: 1,3-DIPOLAR CYCLOADDITION REACTION; 2'-DEOXYCYTIDINE; 3,N-4-ETHENO; Chemistry; Chemistry, Organic; COUMARIN; DNA; FUNCTIONALIZATION; NUCLEOSIDE ANALOGS; PROBE; ZOSTER-VIRUS VZV
Erscheinungsdatum: 2008
Herausgeber: ROYAL SOC CHEMISTRY
Journal: ORGANIC & BIOMOLECULAR CHEMISTRY
Volumen: 6
Ausgabe: 9
Startseite: 1674
Seitenende: 1687
Zusammenfassung: 
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.
ISSN: 14770520
DOI: 10.1039/b719459e

Show full item record

Google ScholarTM

Check

Altmetric