Journal
NUCLEIC ACIDS RESEARCH
Volume 37, Issue 5, Pages 1477-1485Publisher
OXFORD UNIV PRESS
DOI: 10.1093/nar/gkn1066
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Funding
- UCL Chemistry
- UCL Business PLC
- EPSRC [EP/D030005]
- EPSRC [EP/D030005/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/D030005/1] Funding Source: researchfish
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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.
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