Medusamide A, a Panamanian Cyanobacterial Depsipeptide with Multiple β-Amino Acids

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• 作者：Amanda M. Fenner ; Niclas Engene ; Carmenza Spadafora ; William H. Gerwick ; Marcy J. Balunas
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：18
• 期：3
• 页码：352-355
• 全文大小：239K
• ISSN：1523-7052

文摘

From a collection of marine cyanobacteria made in the Coiba National Park along the Pacific coast of the Republic of Panama a novel cyclic depsipeptide, given the trivial name medusamide A, has been isolated and fully characterized. Medusamide A contains four contiguous β-amino acid (2R,3R)-3-amino-2-methylhexanoic acid (Amha) residues. This is the first report of multiple Amha residues and contiguous β-amino acid residues within a single cyclic peptide-type natural product. Stereochemical assignment of the Amha residues was completed following the synthesis of reference standards for this β-amino acid and the subsequent derivatization with Marfey’s reagent and LC–MS analysis.