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Traceless Staudinger Ligation To Introduce Chemical Diversity on β‑Lactamase Inhibitors of Second Generation

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posted on 2021-10-06, 19:09 authored by Flavie Bouchet, Heiner Atze, Michel Arthur, Mélanie Ethève-Quelquejeu, Laura Iannazzo
We explored the traceless Staudinger ligation for the functionalization of the C2 position of second generation β-lactamase inhibitors based on a diazabicyclooctane (DBO) scaffold. Our strategy is based on the synthesis of phosphine phenol esters and their ligation to an azido-containing precursor. Biological evaluation showed that this route provided access to a DBO that proved to be superior to commercial relebactam for inhibition of two of the five β-lactamases that were tested.

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