ArticleNucleic acids research2009
Diene-modified nucleotides for the Diels-Alder-mediated functional tagging of DNA.
Article in Nucleic acids research, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
7 citing papers in PubMed.
- [4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside.RSC chemical biology · 2022Article
- Article
- Versatile Peptide Macrocyclization with Diels-Alder Cycloadditions.Journal of the American Chemical Society · 2019Article
- Article
- 2-Substituted dATP Derivatives as Building Blocks for Polymerase-Catalyzed Synthesis of DNA Modified in the Minor Groove.Angewandte Chemie (International ed. in English) · 2016Article
- DNA modification under mild conditions by Suzuki-Miyaura cross-coupling for the generation of functional probes.Angewandte Chemie (International ed. in English) · 2013Article
- Molecular evolution of functional nucleic acids with chemical modifications.Molecules (Basel, Switzerland) · 2010Review
Corrections and comments
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Authors and funding
2 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We explore the potential of the Diels-Alder cycloaddition for the functional tagging of DNA strands. A deoxyuridine triphosphate derivative carrying a diene at position 5 of the pyrimidine base was synthesized using a two-step procedure. The derivative was efficiently accepted as substrate in enzymatic polymerization assays. Diene carrying strands underwent successful cycloaddition with maleimide-terminated fluorescence dyes and a polymeric reagent. Furthermore, a nucleotide carrying a peptide via a Diels-Alder cyclohexene linkage was prepared and sequence-specifically incorporated into DNA. The Diels-Alder reaction presents a number of positive attributes such as good chemoselectivity, water compatibility, high-yield under mild conditions and no additional reagents apart from a diene and a dienophile. Furthermore, suitable dienophiles are commercially available in the form of maleimide-derivatives of fluorescent dyes and bioaffinity tags. Based on these advantages, diene- and cyclohexene-based nucleotide triphosphates are expected to find wider use in the area of nucleic acid chemistry.
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