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

School of Chemistry

Tel Aviv University

Research output: Contribution to journal › Article › peer-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 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

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol4030138

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title = "Site-selective displacement of tobramycin hydroxyls for preparation of antimicrobial cationic amphiphiles",

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.",

author = "Yifat Berkov-Zrihen and Herzog, \{Ido M.\} and Mark Feldman and Micha Fridman",

year = "2013",

month = dec,

day = "20",

doi = "10.1021/ol4030138",

language = "الإنجليزيّة",

volume = "15",

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journal = "Organic Letters",

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T1 - Site-selective displacement of tobramycin hydroxyls for preparation of antimicrobial cationic amphiphiles

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.

UR - http://www.scopus.com/inward/record.url?scp=84890921786&partnerID=8YFLogxK

U2 - 10.1021/ol4030138

DO - 10.1021/ol4030138

M3 - مقالة

SN - 1523-7060

VL - 15

SP - 6144

EP - 6147

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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