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

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

doi:10.1021/ol4030138

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

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

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 language	English
Pages (from-to)	6144-6147
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	24
DOIs	https://doi.org/10.1021/ol4030138
State	Published - 20 Dec 2013
Externally published	Yes

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10.1021/ol4030138

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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.",

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AU - Berkov-Zrihen, Yifat

AU - Herzog, Ido M.

AU - Feldman, Mark

AU - Fridman, Micha

PY - 2013/12/20

Y1 - 2013/12/20

N2 - 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.

AB - 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.

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JO - Organic Letters

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

Abstract

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