title: Jamaicensamide A, a Peptide Containing β-Amino-α-keto and Thiazole-Homologated η-Amino Acid Residues from the Sponge Plakina jamaicensis.
abstract: A new cyclic peptide, jamaicensamide A, composed of six amino acids, including a thiazole-homologated amino acid, was isolated from the Bahamian sponge Plakina jamaicensis, along with known compounds bitungolide A and franklinolide A. The structure of the title peptide was solved by integrated analysis of MS, 1D and 2D NMR data, oxidation-hydrolyses to α-amino acids, and their stereodetermination by Marfey's method. The close structural resemblance of Western Atlantic-derived jamaicensamide A to known Western Pacific-derived peptides of lithistid sponges in the genus Theonella and Discodermia suggests a common origin: the symbiotic bacterium Entotheonella sp., a so-called "talented producer" responsible for biosynthesis of most Theonella-associated peptides. Similar natural products from sponges of disparate genera evince the likelihood that these invertebrates harbor the same or a very similar symbiont.
authors.affiliation: Department of Chemistry and Biochemistry and ‡Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego , 9500 Gilman Dr. MC-0358, La Jolla, California 92093-0358, United States.
authors.forename: Matthew T
authors.initials: MT
authors.lastname: Jamison
authors.affiliation: Department of Chemistry and Biochemistry and ‡Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego , 9500 Gilman Dr. MC-0358, La Jolla, California 92093-0358, United States.
authors.forename: Tadeusz F
authors.initials: TF
authors.lastname: Molinski
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D000818:Animals; D001444:Bahamas; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification*; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification*; D047232:Theonella / Q000737:chemistry*; D013844:Thiazoles / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D001688:Biological Products; D010456:Peptides, Cyclic; D013844:Thiazoles; C000620737:jamaicensamide A