NDLI: Pyrrolo-dC oligonucleotides bearing alkynyl side chains with terminal triple bonds: synthesis, base pairing and fluorescent dye conjugates prepared by the azide

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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

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Organic & Biomolecular Chemistry Vol - 6 Issue - 8

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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

Content Provider	Royal Society of Chemistry (RSC)
Author	ivolu, Venkata Ramana Seela, Frank
Copyright Year	2008
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 CC 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.
Starting Page	1674
Ending Page	1687
Page Count	14
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	6
Issue Number	9
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b719459e
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Deoxyuridine Umbelliferone Fluorescence Solvolysis Solid-phase synthesis Coumarin Sharpless Ammonia Cycloaddition Alkyl Nucleoside Nucleoside phosphoramidite 1,2,3-Triazole Copper Alkyne
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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8-Aza-7-deazaguanine nucleosides and oligonucleotides with octadiynyl side chains: synthesis, functionalization by the azide-alkyne ‘click’ reaction and nucleobase specific fluorescence quenching of coumarin dye conjugates

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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

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