Aestuaramides, a Natural Library of Cyanobactin Cyclic Peptides Resulting from Isoprene-Derived Claisen Rearrangements

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• 作者：John A. McIntosh ; Zhenjian Lin ; Ma. Diarey B. Tianero ; Eric W. Schmidt
• 刊名：ACS Chemical Biology
• 出版年：2013
• 出版时间：May 17, 2013
• 年：2013
• 卷：8
• 期：5
• 页码：877-883
• 全文大小：320K
• 年卷期：v.8,no.5(May 17, 2013)
• ISSN：1554-8937

文摘

We report 12 cyanobactin cyclic peptides, the aestuaramides, from the cultivated cyanobacterium Lyngbya aestuarii. We show that aestuaramides are synthesized enzymatically as reverse O-prenylated tyrosine ethers that subsequently undergo a Claisen rearrangement to produce forward C-prenylated tyrosine. These results reveal that a nonenzymatic Claisen rearrangement dictates isoprene regiochemistry in a natural system. They also reveal one of the mechanisms that organisms use to generate structurally diverse compound libraries starting from simple ribosomal peptide pathways (RiPPs).