title: A serendipitous discovery of isomotuporin-containing sponge populations of Theonella swinhoei.
abstract: An in-depth LCMS examination of 14 different collections of Indo-Pacific Theonella swinhoei sponges resulted in the discovery of four diastereomeric analogues of the cyclic pentapeptide motuporin. These motuporin analogues all contain a novel 2R configuration for the Adda amino acid. Additionally, one analogue has a unique nonoxygenated Adda amino acid. In all, 15 different compounds were observed by LCMS or isolated. The stereochemistries of the constituent amino acids were determined through a combination of the advanced Marfey technique and 1H NMR data.
authors.affiliation: Department of Chemistry and Biochemistry & Institute of Marine Sciences, University of California, Santa Cruz, California 95064, USA.
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Wegerski
authors.forename: Joshua
authors.initials: J
authors.lastname: Hammond
authors.forename: Karen
authors.initials: K
authors.lastname: Tenney
authors.forename: Teatulohi
authors.initials: T
authors.lastname: Matainaho
authors.forename: Phillip
authors.initials: P
authors.lastname: Crews
mesh_terms: D000818:Animals; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification*; D010781:Photography; D047232:Theonella / Q000737:chemistry*
chemical_list: D010456:Peptides, Cyclic; C093605:motuporin