title: Medusamide A, a Panamanian Cyanobacterial Depsipeptide with Multiple β-Amino Acids.
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.
authors.affiliation: Division of Medicinal Chemistry, Department of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.|Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego , La Jolla, California 92093, United States.|Instituto de Investigaciones Científicas y Servicios de Alta Tecnología (INDICASAT-AIP), City of Knowledge , Apartado 0816-02852, Panama City, Panama.|Smithsonian Tropical Research Institute (STRI) , Ancón, Apartado 0843-03092, Panama.
authors.forename: Amanda M
authors.initials: AM
authors.lastname: Fenner
authors.affiliation: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego , La Jolla, California 92093, United States.|Department of Biological Sciences, Florida International University , Miami, Florida 33199, United States.
authors.forename: Niclas
authors.initials: N
authors.lastname: Engene
authors.affiliation: Instituto de Investigaciones Científicas y Servicios de Alta Tecnología (INDICASAT-AIP), City of Knowledge , Apartado 0816-02852, Panama City, Panama.
authors.forename: Carmenza
authors.initials: C
authors.lastname: Spadafora
authors.affiliation: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego , La Jolla, California 92093, United States.|Smithsonian Tropical Research Institute (STRI) , Ancón, Apartado 0843-03092, Panama.
authors.forename: William H
authors.initials: WH
authors.lastname: Gerwick
authors.affiliation: Division of Medicinal Chemistry, Department of Pharmaceutical Sciences, University of Connecticut , Storrs, Connecticut 06269, United States.|Instituto de Investigaciones Científicas y Servicios de Alta Tecnología (INDICASAT-AIP), City of Knowledge , Apartado 0816-02852, Panama City, Panama.|Smithsonian Tropical Research Institute (STRI) , Ancón, Apartado 0843-03092, Panama.
authors.forename: Marcy J
authors.initials: MJ
authors.lastname: Balunas
mesh_terms: D000614:Aminocaproates / Q000737:chemistry; D000458:Cyanobacteria / Q000737:chemistry*; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010176:Panama; D013237:Stereoisomerism
chemical_list: D000614:Aminocaproates; D047630:Depsipeptides; C000608184:medusamide A; C023325:2-amino-5-methyl-5-hexenoic acid