Studies on Glucosaccharolactones

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Abstract
Crystalline glucosaccharo-1:4, 3:6-dilactone was synthesized. The apparent inhibitory effect of this dilactone on β-glucuronidase was one fifth that of SL1:4. The inhibition of β-glucuronidase by acids derived from glucose and their lactone decreased in the following order. SL1:4>SDL>SA>SL3:6>glucuronic acid > glucono-γ-lactone > glucono-δ-lactone ≥ gluconate = glucuronolactone. The inhibitory effect of the compounds aving a 1:4-lactone ring was more powerful than that of the corresponding acids, while the 3:6-lactonized compounds were less inibitory than the corresponding acids. Glucosaccharo-1: 4, 3:6-dilactone in aqueous solution was unstable and decomposed spontaneously producing SL1:4, SL3:6 and SA. The relationship between its stability and its apparent inhibitory effect on β-glucuronidase was discussed.