Natural products, fluorinated 4-fluorothreonine

M.R. Amin, D.B. Harper, J.M. Moloney, C.D. Murphy, J.A.K. Howard, D. O Hagan, A short highly stereoselective synthesis of the fluorinated natural product (2S,3S)-4-fluorothreonine, Chem. Comm. (1997) 1471-1472. 

Amin MR, Harper DB, Moloney JM, Murphy CD, Howard JAK, O Hagan D (1997) A Short Highly Stereoselective Synthesis of the Fluorinated Natural Product (2S,3S)-4-Fluorothreonine. Chem Commun 1471... 

Murphy CD, Schaffrath C, O Hagan D (2003) Fluorinated Natural Products The Biosynthesis of Fluoroacetate and 4-Fluorothreonine in Streptomyces cattleya. Chemosphere 52 455... 

Organofluorines play an important role in medicinal chemistry, and estimates indicate that 20-30% of the pharmaceutical products on the market contain at least one fluorine atom [57, 58], However, natural organofluorine compounds are exceedingly rare, and the pharmaceutical industry has not yet benefited from a microbial source of such compounds. The soil bacterium Streptomyces cattleya was found to produce fluoro-acetate and 4-fluorothreonine, but the biological scope is limited to a single biological pathway that produces fluoroace-tate [58, 59], Identification of the fluorination enzyme FIA, responsible for C-F bond formation in S. cattleya, enabled the directed manipulation of biosynthetic pathways for the formation of fluorinated natural products. 

Murphy, C.D., Schaffrath, C., and O Hagan, D. (2003) Fluorinated natural products the biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya. Chemosphere, 52, 455 161. 

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