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Updated: Jul 12, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Theoretically Predicted and Experimentally Detected Chirality of Dibenzocyclooctynes and Their Triazole Adducts with
Giulia Mazzoccanti1, Roberta Franzini1, Alessia Ciogli1
1Department of Chemistry and Technology of Drugs, Excellence 2018-2022, Sapienza University of Rome, P.le Aldo Moro 5, Rome 00185, Italy.
Abstract:
Dibenzocyclooctynes have emerged as promising scaffolds for bioorthogonal ligation. An important structural aspect that has not been addressed so far relates to their chirality. Herein, we explore, by theoretical and experimental methods, this structural aspect that has been neglected so far. First, computational analysis is conducted, and the results are used as a guide for the experimental investigation. Next, an array of different experiments (high-performance liquid chromatography (HPLC) on chiral columns, chiroptical spectroscopy, and X-ray diffraction) for structure elucidation is scrutinized in concert. Finally, this work demonstrates the chirality and the stereodynamic behavior of dibenzocyclooctynes and their triazole derivatives with simple azides and also uncovers their conformational behavior.
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