Synthesis of L-idaro-1,4-lactone, an inhibitor of alpha-L-idosiduronase.
L-idaro-1,4-lactone was synthesized by two different, published methods: (1) epimerization of monopotassium D-glucarate by refluxing in aqueous barium hydroxide, and (2) oxidation of L-iditol by heating in dilute nitric acid. The lactone, formed by heat dehydration from aqueous solution at low pH, was purified by paper chromatography, and quantitated by gas-liquid chromatography using inositol as the internal standard. The monolactone inhibited human, seminal-fluid alpha-L-idosiduronase activity, with either phenyl or 4-methylumbelliferyl alpha-L-idosiduronic acid as the substrate, to the same degree as D-glucaro-1,4-lactone inhibits alpha-D-glucosiduronase.
D005937:Glucaric Acid / Q000031:analogs & derivatives; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D006801:Humans; D007068:Iduronidase / Q000037:antagonists & inhibitors*; D007202:Indicators and Reagents; D007700:Kinetics; D007783:Lactones / Q000138:chemical synthesis / Q000494:pharmacology; D008297:Male; D012661:Semen / Q000201:enzymology; D013379:Substrate Specificity; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000494:pharmacology
D007202:Indicators and Reagents; D007783:Lactones; D013400:Sugar Acids; C009194:saccharolactone; D006026:Glycoside Hydrolases; D007068:Iduronidase; D005937:Glucaric Acid