The fluorocitrate isomer that is a strong inhibitor and inactivator of aconitase has been shown by x-ray crystallographic studies on the rubidium ammonium salt to have the configurations (1R : 2R) or (1S : 2S) 1-fluoro-2-hydroxy-1,2,3-propanetricarboxylic acid. A possible mechanism for the action of fluorocitrate is proposed which involves the 1R : 2R isomer suggested from biochemical data.
During the study of possible synthetic routes to a pyridine analog of Chloromycetin2 3several nitropyridine derivatives were prepared. 5-Nitropyridine-2-carboxaldehyde was prepared by the selenium dioxide oxidation of 2-methyl-5-nitropyridine but the yield was low and this approach was not followed further. 2-Nitropyridine-5-carboxylic acid was prepared and its esterification and subsequent use in ester-type condensations was investigated. The 2-nitro group proved to be very labile toward nucleophilic substitution. It was replaced by chloro, hydroxy, methoxy, and amino groups with ease.
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