Related Experiment Videos
Medusamide A, a Panamanian Cyanobacterial Depsipeptide with Multiple β-Amino Acids
Amanda M Fenner1,2,3,4, Niclas Engene2,5, Carmenza Spadafora3
1Division of Medicinal Chemistry, Department of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.
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.