Everybody thinks about DBCO functionality as a copper-less click chemistry partner.
But the authors of this paper https://doi.org/10.1002/anie.202009408
have demonstrated strange behavior of very familiar reagent under specific conditions and in the presence of the Silver Triflate catalyst (AgNTf2).
This work comes from the group of Prof. W. Huang at University of Chinese Academy of Sciences in Beijing.
They saw that DBCO rearranges into very conjugated structure and transfers it’s acyl fragment to any available amine, very often Lysine side chain.
This works with a lot of biological object as well, e.g. peptides, proteins and even viruses. Obviously under very mild conditions, slightly acidic pH and room temperature.
The mechanism seems to be pretty intuitive, and yet it is hard to believe that it works under such mild conditions.
Please let me know if anybody has tried it and if it has worked for you.
Because I know some people that have tried it and it did not work.
Supplementary materials are available to download here: https://onlinelibrary.wiley.com/action/downloadSupplement?doi=10.1002%2Fanie.202009408&file=anie202009408-sup-0001-misc_information.pdf