In recent years, the Glaser-Hay coupling reaction has emerged as an efficient and effective way to create therapeutic bioconjugates. Through the utilization of unnatural amino acids, well-defined homogenous bioconjugates can be produced, furthering the feasibility and application of these molecules in drug delivery or chemical imaging. Herein, we report the investigation of the mechanism of the Glaser-Hay to facilitate optimization under biological conditions. Several ligands were evaluated on their ability to minimize protein oxidation and improve coupling efficiency. From this work, we were able to understand the mechanism of the Glaser-Hay in aqueous media. Further, we discovered promising ligands that reduce protein damage and developed two novel strategies to streamline the preparation/purification of bioconjugates containing unnatural amino acids.

Mechanistic investigation and further optimization of the aqueous Glaser-Hay bioconjugation

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.