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

Author:
Fenner, Amanda M., Engene, Niclas, Spadafora, Carmenza, Gerwick, William H., Balunas, Marcy J.
Source:
Organic letters 2016 v.18 no.3 pp. 352-355
ISSN:
1523-7052
Subject:
Cyanobacteria, amino acids, chemical structure, coasts, derivatization, liquid chromatography, mass spectrometry, national parks, organic compounds, reference standards, stereochemistry, Panama
Abstract:
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.
Agid:
5792259