Facile Synthesis of Tetrafluorotyrosine and Its Application in pH Triggered Membrane Lysis

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• 作者：Fang Wang ; Luoheng Qin ; Patrick Wong ; Jianmin Gao
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：January 21, 2011
• 年：2011
• 卷：13
• 期：2
• 页码：236-239
• 全文大小：196K
• 年卷期：v.13,no.2(January 21, 2011)
• ISSN：1523-7052

文摘

鈥淪mart鈥?peptides that lyse membranes in response to biological stimuli are of considerable interest. Herein, we report a facile synthesis of l-tetrafluorotyrosine (l-f₄Y) and its utilization as a pH sensing element. The synthetic route affords gram quantities of l-f₄Y within two days. Incorporation of this unnatural amino acid into magainin 2 gives a peptide that turns on its membrane-lytic activity upon mild acidification.