Glyoxal-Linked Nucleotides and DNA for Bioconjugations and Crosslinking with Arginine-Containing Peptides and Proteins

0556689 - ÚOCHB 2023 RIV DE eng J - Journal Article
Leone, Denise Liu - Pohl, Radek - Hubálek, Martin - Kadeřábková, Marta - Krömer, Matouš - Sýkorová, Veronika - Hocek, Michal
Glyoxal-Linked Nucleotides and DNA for Bioconjugations and Crosslinking with Arginine-Containing Peptides and Proteins.
Chemistry - A European Journal. Roč. 28, č. 14 (2022), č. článku e202104208. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA ČR(CZ) GA18-03305S; GA MŠMT(CZ) EF16_019/0000729
Grant - others:AV ČR(CZ) AP1501
Program: Akademická prémie - Praemium Academiae
Institutional support: RVO:61388963
Keywords : bioconjugations * crosslinking * DNA * glyoxal * nucleotides
OECD category: Biochemistry and molecular biology
Impact factor: 4.3, year: 2022
Method of publishing: Limited access
https://doi.org/10.1002/chem.202104208

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 ordUTP. 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.
Permanent Link: http://hdl.handle.net/11104/0330810