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Site-Selective Palladium-catalyzed Oxidation of Unprotected Aminoglycosides and Sugar Phosphates.

Nittert MarinusNiels R M ReintjensKlara HaldimannMarc L M C MouthaanSven N HobbieMartin D WitteAdriaan J Minnaard
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2024)
The site-selective modification of complex biomolecules by transition metal-catalysis is highly warranted, but often thwarted by the presence of Lewis basic functional groups. This study demonstrates that protonation of amines and phosphates in carbohydrates circumvents catalyst inhibition in palladium-catalyzed site-selective oxidation. Both aminoglycosides and sugar phosphates, compound classes that up till now largely escaped direct modification, are oxidized with good efficiency. Site-selective oxidation of kanamycin and amikacin was used to prepare a set of 3'-modified aminoglycoside derivatives of which two showed promising activity against antibiotic-resistant E. coli strains.
Keyphrases
  • carbon dioxide
  • escherichia coli
  • hydrogen peroxide
  • transition metal
  • visible light
  • pseudomonas aeruginosa
  • multidrug resistant
  • drug resistant
  • acinetobacter baumannii
  • room temperature
  • ionic liquid
  • highly efficient