Issue 13, 2019

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

Abstract

The Glaser−Hay bioconjugation has recently emerged as an efficient and attractive method to generate stable, useful bioconjugates with numerous applications, specifically in the field of therapeutics. Herein, we investigate the mechanism of the aqueous Glaser−Hay coupling to better understand optimization strategies. In doing so, it was identified that catalase is able to minimize protein oxidation and improve coupling efficiency, suggesting that hydrogen peroxide is produced during the aqueous Glaser−Hay bioconjugation. Further, several new ligands were investigated to minimize protein oxidation and maximize coupling efficiency. Finally, two novel strategies to streamline the Glaser−Hay bioconjugation and eliminate the need for secondary purification have been developed.

Graphical abstract: Mechanistic investigation and further optimization of the aqueous Glaser−Hay bioconjugation

Supplementary files

Article information

Article type
Paper
Submitted
09 Feb 2019
Accepted
06 Mar 2019
First published
06 Mar 2019

Org. Biomol. Chem., 2019,17, 3396-3402

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

C. R. Travis, L. E. Mazur, E. M. Peairs, G. H. Gaunt and D. D. Young, Org. Biomol. Chem., 2019, 17, 3396 DOI: 10.1039/C9OB00327D

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