期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 28, 期 14, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202104208
关键词
bioconjugations; crosslinking; DNA; glyoxal; nucleotides
资金
- Czech Academy of Sciences (Praemium Academiae award)
- Czech Science Foundation [18-03305S]
- European Regional Development Fund
- OP RDE [CZ.02.1.01/0.0/0.0/16_019/0000729]
Glyoxal-linked nucleotides were synthesized and used for efficient bioconjugations and crosslinking with arginine-containing peptides or proteins. The reactive glyoxal modification in DNA was found to be more reactive than previously reported 1,3-diketone-linked DNA probes.
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.
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