Abstract
2,5-Anhydro-1-deoxy- d-mannitol ( 4), 2,5-anhydro-1-deoxy- d-talitol ( 8), and 2,5-anhydro-1-deoxy- d-lyxitol ( 12) were prepared by Raney-nickel desulfurization of 2,5-anhydro- d-mannose dihexyl dithioacetal ( 3), 2,5-anhydro- d-talose dihexyl dithioacetal ( 7), and 2,5-anhydro- d-lyxose diethyl dithioacetal ( 11), respectively, in 64% yield based on starting thioacetal. Compounds 3 and 7 were prepared in 42% yield, by the acid-catalyzed condensation of 2,5-anhydro- d-mannose and 2,5-anhydro- d-talose, respectively, with hexanethiol. Compound 11 was prepared in 66% yield, by treatment of d-lyxose diethyl dithioacetal with p-toluenesulfonyl chloride-pyridine. Compounds 4, 8, and 12 were examined as substrates and inhibitors for yeast hexokinase and bovine-liver fructokinase. Hexokinase and fructokinase phosphorylated 4 with K m values of 25 and 1.94m m, and V max ( 4)/ V max ( d-fructose) 0.007 and 0.13, respectively. Fructokinase was competitively inhibited by 8 and 12, with K i values of 17 and 99m m, respectively.
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