title: Biosynthesis of fluorothreonine and fluoroacetic acid by the thienamycin producer, Streptomyces cattleya.
abstract: An antimetabolite, THX, was isolated from fermentation broths of the thienamycin producer, Streptomyces cattleya, when the organism was grown in the presence of a fluorine-containing substrate. THX was subsequently identified as one of the four possible stereoisomers of 4-fluorothreonine. Inorganic fluoride or any one of a number of organofluorine compounds can be used as precursors of 4-fluorothreonine. In addition, 19F NMR has provided evidence that the organism synthesizes fluoroacetate under the same fermentation conditions. The in vitro antibacterial spectrum of 4-fluorothreonine is also presented.
authors.forename: M
authors.initials: M
authors.lastname: Sanada
authors.forename: T
authors.initials: T
authors.lastname: Miyano
authors.forename: S
authors.initials: S
authors.lastname: Iwadare
authors.forename: J M
authors.initials: JM
authors.lastname: Williamson
authors.forename: B H
authors.initials: BH
authors.lastname: Arison
authors.forename: J L
authors.initials: JL
authors.lastname: Smith
authors.forename: A W
authors.initials: AW
authors.lastname: Douglas
authors.forename: J M
authors.initials: JM
authors.lastname: Liesch
authors.forename: E
authors.initials: E
authors.lastname: Inamine
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000302:isolation & purification* / Q000494:pharmacology; D000963:Antimetabolites / Q000302:isolation & purification* / Q000494:pharmacology; D001424:Bacterial Infections / Q000188:drug therapy; D005463:Fluoroacetates / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D013237:Stereoisomerism; D013302:Streptomyces / Q000378:metabolism*; D013845:Thienamycins / Q000096:biosynthesis*; D013912:Threonine / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D000963:Antimetabolites; D005463:Fluoroacetates; D013845:Thienamycins; C048271:4-fluorothreonine; D013912:Threonine; C014815:fluoroacetic acid; C015537:thienamycin