title: De novo synthesis of benzosceptrin C and nagelamide H from 7-15N-oroidin: implications for pyrrole-aminoimidazole alkaloid biosynthesis.
abstract: De novo synthesis of the natural products benzosceptrin C (7) and nagelamide H (8) was achieved using cell-free enzyme preparations from the marine sponges Agelas sceptrum and Stylissa caribica employing synthetic 7-(15)N-oroidin. These studies provide direct experimental evidence to support the long-standing, but untested, hypothesis that oroidin is a precursor to more complex pyrrole-aminoimidazole alkaloids, such as the sceptrins, benzosceptrins, and nagelamides. In addition, a new nagelamide, didebromonagelamide A (5b), was isolated from S. caribica, representing the first report of a nagelamide-like compound from the Caribbean.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
authors.forename: E Paige
authors.initials: EP
authors.lastname: Stout
authors.forename: Brandon I
authors.initials: BI
authors.lastname: Morinaka
authors.forename: Yong-Gang
authors.initials: YG
authors.lastname: Wang
authors.forename: Daniel
authors.initials: D
authors.lastname: Romo
authors.forename: Tadeusz F
authors.initials: TF
authors.lastname: Molinski
mesh_terms: D047230:Agelas / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D017691:Caribbean Region; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D007093:Imidazoles; D011758:Pyrroles; C549721:benzosceptrin C; C573515:didebromonagelamide A; C573514:nagelamide H; C077209:oroidin