Site-selective displacement of tobramycin hydroxyls for preparation of antimicrobial cationic amphiphiles

Yifat Berkov-Zrihen, Ido M. Herzog, Mark Feldman, Micha Fridman

Research output: Contribution to journalArticlepeer-review

Abstract

A short site-selective strategy for the activation and derivatization of alcohols of the clinically important aminoglycoside tobramycin is reported. The choice of amine protecting group affected the site-selective conversion of secondary alcohols of tobramycin into leaving groups. Temperature-dependent, chemoselective sequential nucleophilic displacements resulted in hetero- and homodithioether tobramycin-based cationic amphiphiles that demonstrated marked antimicrobial activity and impressive membrane selectivity.

Original languageEnglish
Pages (from-to)6144-6147
Number of pages4
JournalOrganic Letters
Volume15
Issue number24
DOIs
StatePublished - 20 Dec 2013

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