Biosynthesis of fluoroacetate and 4-fluorothreonine by Streptomyces cattleya. The stereochemical processing of glycerol

When both (2R)-[1-H-2(2)]- and (2S)-[1-H-2(2)]-glycerol are incubated with resting cell suspensions of S. cattleya, only the 2R-enantiomer labels the fluoromethyl groups of fluoroacetate and 4-fluorothreonine, with retention of both deuterium atoms, placing metabolic and mechanistic limitations on the process of biological fluorination.