title: Biosynthetic studies of the notoamides: isotopic synthesis of stephacidin A and incorporation into notoamide B and sclerotiamide.
abstract: The advanced natural product stephacidin A is proposed as a biosynthetic precursor to notoamide B in various Aspergillus species. Doubly (13)C-labeled racemic stephacidin A was synthesized and fed to cultures of the terrestrial-derived fungus, Aspergillus versicolor NRRL 35600, and the marine-derived fungus, Aspergillus sp. MF297-2. Analysis of the metabolites revealed enantiospecific incorporation of intact (-)-stephacidin A into (+)-notoamide B in Aspergillus versicolor and (+)-stephacidin A into (-)-notoamide B in Aspergillus sp. MF297-2. (13)C-Labeled sclerotiamide was also isolated from both fungal cultures.
authors.affiliation: Department of Chemistry, Colorado State University, 1301 Center Avenue, Fort Collins, Colorado 80523, USA.
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Finefield
authors.forename: Hikaru
authors.initials: H
authors.lastname: Kato
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Greshock
authors.forename: David H
authors.initials: DH
authors.lastname: Sherman
authors.forename: Sachiko
authors.initials: S
authors.lastname: Tsukamoto
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
mesh_terms: D001230:Aspergillus / Q000737:chemistry* / Q000378:metabolism; D001688:Biological Products / Q000737:chemistry* / Q000378:metabolism; D002247:Carbon Isotopes / Q000737:chemistry / Q000378:metabolism; D026121:Indole Alkaloids / Q000737:chemistry* / Q000378:metabolism; D007212:Indolizines / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry* / Q000378:metabolism
chemical_list: D001688:Biological Products; D002247:Carbon Isotopes; D026121:Indole Alkaloids; D007212:Indolizines; D013141:Spiro Compounds; C520596:notoamide B; C103459:sclerotiamide; C470895:stephacidin A