Biosynthesis of fluorothreonine and fluoroacetic acid by the thienamycin producer, Streptomyces cattleya.
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.
Sanada
M
M
Miyano
T
T
Iwadare
S
S
Williamson
J M
JM
Arison
B H
BH
Smith
J L
JL
Douglas
A W
AW
Liesch
J M
JM
Inamine
E
E
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
D000900:Anti-Bacterial Agents; D000963:Antimetabolites; D005463:Fluoroacetates; D013845:Thienamycins; C048271:4-fluorothreonine; D013912:Threonine; C014815:fluoroacetic acid; C015537:thienamycin