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Diene-modified nucleotides for the DielsAlder-mediated functional tagging of DNA

Borsenberger, V; Howorka, S; (2009) Diene-modified nucleotides for the DielsAlder-mediated functional tagging of DNA. Nucleic Acids Research , 37 (5) 1477 - 1485. 10.1093/nar/gkn1066. Green and gold open access

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Abstract

We explore the potential of the DielsAlder 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 DielsAlder cyclohexene linkage was prepared and sequence-specifically incorporated into DNA. The DielsAlder 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.

Type:Article
Title:Diene-modified nucleotides for the DielsAlder-mediated functional tagging of DNA
Open access status:An open access publication. A version is also available from UCL Discovery.
DOI:10.1093/nar/gkn1066
Publisher version:http://dx.doi.org/10.1093/nar/gkn1066
Language:English
Additional information:The online version of this article has been published under an open access model. Users are entitled to use, reproduce, disseminate, or display the open access version of this article for non-commercial purposes provided that: the original authorship is properly and fully attributed; the Journal and Oxford University Press are attributed as the original place of publication with the correct citation details given; if an article is subsequently reproduced or disseminated not in its entirety but only in part or as a derivative work this must be clearly indicated. For commercial re-use, please contact journals.permissions@oupjournals.org
Keywords:Alder, oligonucleotides, 5'-triphosphates, cycloaddition, nucleosides, protein, acids
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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