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.
MeSH terms
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Animals
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Anti-Bacterial Agents / isolation & purification*
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Anti-Bacterial Agents / pharmacology
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Antimetabolites / isolation & purification*
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Antimetabolites / pharmacology
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Bacterial Infections / drug therapy
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Fluoroacetates / metabolism*
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Magnetic Resonance Spectroscopy
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Mice
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Pseudomonas aeruginosa / drug effects
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Stereoisomerism
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Streptomyces / metabolism*
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Thienamycins / biosynthesis*
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Threonine / analogs & derivatives*
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Threonine / biosynthesis
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Threonine / pharmacology
Substances
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Anti-Bacterial Agents
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Antimetabolites
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Fluoroacetates
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Thienamycins
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4-fluorothreonine
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Threonine
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fluoroacetic acid
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thienamycin