Investigating Bicyclobutane-Triazolinedione Cycloadditions as a Tool for Peptide Modification

Acyl bicyclobutanes are shown to engage in strain promoted cycloaddition reactions with a diverse array of triazolinedione reagents. The synthesis of an orthogonally protected urazole building block enabled the facile preparation of amino acid and peptide-derived triazolinediones that undergo cycloaddition reactions to afford novel peptide conjugates. The additive-free and fully atom-economical nature of the transformation is a promising starting point for the generalization of this cycloaddition reaction for the functionalization of biomolecules.

Automated summary

This study investigates the strain promoted cycloaddition reactions of acyl bicyclobutanes with triazolinedione reagents. The synthesis of novel peptide conjugates through cycloaddition reactions is facilitated by the orthogonally protected urazole building block. The additive-free and fully atom-economical nature of this transformation provides a promising starting point for the functionalization of biomolecules.