One type of oligonucleotide modification, the maleimide group, has seen expanded use in bioconjugation owing to its dual utility in bioorthogonal reactions, the classical Michael-addition, and now in the [4+2] cycloaddition reaction. Recently, a more comprehensive understanding of the thioether linkage with maleimide offers further improved stabilization of this linkage.
This application note from Glen Research expands on the “click chemistry” opportunities of maleimide used for chemoselective aqueous bioconjugations. Thus, the focus will turn towards advances in bioconjugation of maleimide modified oligonucleotides with a) thiol- and b) diene-containing reactants, and their two differing click chemistries. Using published data, results are highlighted that demonstrate the negligible reactivity of thiophosphates with the maleimide group and the additional utility of the maleimide group in the Diels-Alder cycloaddition. These results provide support for use of the 5’-maleimide modifier to prepare stable ODN-bioconjugates, including therapeutic oligonucleotide conjugates.
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