Is the Thiol-Maleimide Reaction a Click Chemistry Reaction?

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Maleimide Click Chemistry

Glen Research provides linker-, spacer-, and modified base-phosphoramidites to assist researchers assembling oligonucleotide (ODN) bioconjugates.  One type of ODN modification, the maleimide group, has found expanded use in bioconjugation from its dual utility in bioorthogonal reactions.


During synthesis, the maleimide group cannot be directly incorporated into an oligo because it is not stable to ammonia deprotection conditions. However, using 5’-Maleimide-Modifier Phosphoramidite to introduce a latent maleimide during synthesis permits a retro-Diels-Alder reaction carried out during workup, to convert the modifier to a 5’-maleimide group. 

Download this note for a look at:

  • Click chemistry opportunities of maleimide used for chemoselective aqueous bioconjugations
  • Advances in bioconjugation of maleimide modified oligonucleotides with thiol- and diene-containing reactants
  • Additional utility of the maleimide group in the Diels-Alder cycloaddition
  • Use of the 5’-maleimide modifier to prepare stable ODN-bioconjugates, including therapeutic oligonucleotide conjugates
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