Site‐Selective Palladium‐catalyzed Oxidation of Unprotected Aminoglycosides and Sugar Phosphates

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 pallad...

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Bibliographic Details
Published in:Chemistry : a European journal 2024-04, Vol.30 (19), p.e202400017-n/a
Main Authors: Marinus, Nittert, Reintjens, Niels R. M., Haldimann, Klara, Mouthaan, Marc L. M. C., Hobbie, Sven N., Witte, Martin D., Minnaard, Adriaan J.
Format: Article
Language:English
Subjects:
Amikacin
Amines
Aminoglycoside antibiotics
Aminoglycosides
antibiotics
Biomolecules
Carbohydrates
Catalysis
Catalysts
E coli
Functional groups
Kanamycin
Oxidation
Palladium
Phosphates
Protonation
site-selective
Sugar
Transition metals
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Summary: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. Protonation of amino groups and phosphates in aminoglycosides and sugar phosphates allows direct palladium‐catalyzed site‐selective oxidation without the use of protecting groups. The site‐selective oxidation of kanamycin and amikacin allowed the preparation of a set of 3’‐modified aminoglycoside derivatives of which two show promising activity against antibiotic‐resistant E. coli strains.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202400017