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

Seela, Frank; Xiong, Hai; Leonard, Peter; Budow, Simone

doi:10.1039/b822041g

Cited by 50 publications

(60 citation statements)

References 44 publications

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“…5). 28 Pyrazolo [3,4-d]pyrimidine nucleoside derivative 15 shows a much higher fluorescence intensity than that of the corresponding pyrrolo[2,3-d]pyrimidine derivative 16. The quenching in the dye conjugate 16 was found to be stronger with monomeric nucleoside conjugates than in single-stranded or duplex DNA.…”

Section: Oligonucleotide Labelling With Fluorophores and Carbohydratesmentioning

confidence: 99%

Click chemistry with DNA

2010

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Section: Oligonucleotide Labelling With Fluorophores and Carbohydratesmentioning

confidence: 99%

Click chemistry with DNA

2010

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“…The preferred positions at which to attach an alkyne moiety to an oligonucleotide are position 5 in the pyrimidine system (e.g., 1 , Scheme ),17 position 7 in the 7‐deazapurine system (e.g., 2 , as substitutes for normal purines),18 and position 2′ in ribofuranoside components (e.g., 3 ) 15. 19 Acetylenes as reactive groups at these representative positions are accepted by DNA polymerases in primer extension experiments and PCR 14b.…”

Section: Copper‐catalyzed Azide–alkyne Cycloaddition (Cuaac) and Tmentioning

confidence: 99%

Copper‐Free Postsynthetic Labeling of Nucleic Acids by Means of Bioorthogonal Reactions

et al. 2015

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Postsynthetic modification of nucleic acids has the advantage that the chemical development of only a few building blocks is necessary, each bearing a chosen reactive functional group that is applicable to its reactive counterpart for a variety of different labeling types. The reactive group is either linked to phosphoramidites for chemical synthesis on solid phase or attached to nucleoside triphosphates for application in primer extension experiments and PCR. Chemoselectivity is required for this strategy, together with bioorthogonality to perform these labelings in living cells or even organisms. Currently, the copper-free reactions include strain-promoted 1,3-dipolar cycloadditions, "photoclick" reactions, Diels-Alder reactions with inverse electron demand, and nucleophilic additions. The majority of these modification strategies show good to excellent reaction kinetics, an important prerequisite for labeling inside cells and in vivo in order to keep the concentrations of the reacting partners as low as possible.

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“…Likewise the "click" reaction was performed on the 7deazapurine 2'-deoxyribonucleosides 99a, 100a,f and 102f to afford various fluorescent "click" conjugates (123)(124)(125)(126)(127)(128)(129) (Fig. 19) [140,145,146,149,178,[180][181][182]. 7-Deazapurine "click" conjugates were also subjected to fluorescence studies [139,140,145,146,181,182].…”

Section: Functionalization Of 7-deazapurine 2'-deoxyribonucleosides Ementioning

confidence: 99%

7-Deazapurine (Pyrrolo[2,3-d]pyrimidine) 2-Deoxyribonucleosides: Syntheses and Transformations

Seela¹,

Budow²,

Peng

2012

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This review reports on the synthesis of 7-deazapurine (pyrrolo[2,3-d]pyrimidine) 2'-deoxyribonucleosides, including-D-and-L-enantiomers, fluoro derivatives, and 2',3'-dideoxyribonucleosides. It covers the various aspects of convergent nucleoside synthesis. Stereochemically defined-D and-L 2'-deoxyribonucleosides as well as sugar derivatives were prepared by nucleobase anion glycosylation. This glycosylation reaction is regioselective for the pyrrole nitrogen and stereoselective for-nucleoside formation. Common glycosylation protocols lead to 7-deazapurine 2'-deoxyribonucleosides with unusual glycosylation sites. 7-Deazapurine 2',3'dideoxyribonucleosides were also obtained from 2'-deoxy-or 3'-deoxyribonucleosides by Barton-McCombie deoxygenation, by elimination of sugar hydroxyl groups or by anion glycosylation. Another aspect of the review is the functionalization of pyrrolo[2,3-d]pyrimidine nucleosides. A broad range of reporter groups were introduced by the Sonogashira cross coupling or the copper(I)-catalyzed Huisgen-Meldal-Sharpless "click" reaction. The application of 7-deazapurine nucleosides as antiviral or anticancer agents, and the use of 7deazapurine nucleoside triphosphates in the Sanger dideoxy DNA-sequencing are also reported.

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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

Cited by 50 publications

References 44 publications

Click chemistry with DNA

Click chemistry with DNA

Copper‐Free Postsynthetic Labeling of Nucleic Acids by Means of Bioorthogonal Reactions

7-Deazapurine (Pyrrolo[2,3-d]pyrimidine) 2-Deoxyribonucleosides: Syntheses and Transformations

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