Short Communications

Abstract

The biochemical significance of 'lethal synthesis' has been repeatedly emphasized by Peters (1963) and this has undoubtedly provided the rationale for the synthesis of a wide range of fluorinated analogues in the steroid (reviewed by Taylor & Kent, 1965), carboxylic acid (Pattison, 1959) and heterocyclic (e.g. 5-fluorouracil; Hartman & Heidelberger, 1961) fields in which hydrogen has been replaced by fluorine. Comparative physicochemical studies with 6deoxy-6-fluoro-D-galactose (Kent, Morris & Taylor, 1960) and X-ray crystallographic studies with 2-deoxy-2-fluoroerythritol and erythritol (Bekoe & Powell, 1959) show that only minor differences in physical and chemical properties result when a hydroxyl group is replaced by fluorine in these compounds. These results, together with the similarity in size and electronegativity between the hydroxyl group and fluorine, suggest the possibility that suitably substituted fluoro sugars and related compounds might provide new inhibitors of carbohydrate metabolism. Biochemical studies already reported with 2-deoxy-2-fluoroerythritol (Smith, Anderson, Keppie, Kent & Timmis, 1965), which acts as a growth inhibitor of Brucella abortus, and 2-deoxy-2-fluoroglycerol (O'Brien & Peters, 1958) support this suggestion. It is only recently, however, that fluoropentoses (Wright & Taylor, 1967) and fluorohexoses (Buck, Foster, Hems & Weber, 1966) with fluorine in other than the anomeric (reviewed by Michael & Klemer, 1961) or terminal positions (Taylor & Kent, 1958) of monosaccharides have become available.We now report some preliminary biochemical results with 3FG* (Buck et al. 1966). The structure of this compound has been established (Foster, Hems & Weber, 1967) by degradation to the known 3-deoxy-3-fluoro-D-xylose (Wright & Taylor, 1967).Materials and methods. 3FG was a gift from Professor A. B. Foster and Mr R. Hems. C02 evolution, determined by the method of Johnson (Umbreit, Burris & Stauffer, 1964), and oxygen uptake were measured in a Warburg respirometer. The extent of respiration was determined by continuing the experiments until