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Glyoxal-linked 2'-deoxyuridine 5'-O-mono- and triphosphates were synthesized through a CuAAC click reaction of 4-azidophenylglyoxal or a Sonogashira reaction of 4-bromophenylglyoxal with 5-ethynyl-dUMP or -dUTP. The triphosphates were used as substrates for enzymatic synthesis of modified DNA probes with KOD XL DNA polymerase. The glyoxal-linked nucleotides reacted with arginine-containing peptides to form stable imizadolone-linked conjugates. This reactive glyoxal modification in DNA was used for efficient bioconjugations and crosslinking with Arg-containing peptides or proteins (e. g., histones) and was found to be more reactive than previously reported 1,3-diketone-linked DNA probes. © 2022 Wiley-VCH GmbH.

Citation

Denise-Liu' Leone, Radek Pohl, Martin Hubálek, Marta Kadeřábková, Matouš Krömer, Veronika Sýkorová, Michal Hocek. Glyoxal-Linked Nucleotides and DNA for Bioconjugations and Crosslinking with Arginine-Containing Peptides and Proteins. Chemistry (Weinheim an der Bergstrasse, Germany). 2022 Mar 07;28(14):e202104208

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PMID: 35076143

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