Site-Selective Displacement of Tobramycin Hydroxyls for Preparation of Antimicrobial Cationic Amphiphiles

详细信息    查看全文

• 作者：Yifat Berkov-Zrihen ; Ido M. Herzog ; Mark Feldman ; Micha Fridman
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：December 20, 2013
• 年：2013
• 卷：15
• 期：24
• 页码：6144-6147
• 全文大小：288K
• 年卷期：v.15,no.24(December 20, 2013)
• ISSN：1523-7052

文摘

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.