Hydrolytic properties of N-sulfated compounds containing neighboring hydroxyl or sulfate groups, with reference to chemical properties of natural heparin

Abstract

Hydrolytic properties of synthetic acyclic and cyclic sulfoamino compounds having a neighboring hydroxyl or O-sulfate group were examined. In all the compounds examined, the O-sulfate group in vicinal position accelerated the hydrolysis of the sulfoamino group more than did the hydroxyl group in vicinal position, and the hydrolysis of the sulfoamino group linked to a cyclic compound was faster than that of a group linked to an acyclic compound, with the substituent in trans position having a greater effect than that in cis position. The effect of a substituent removed by one carbon atom from the sulfoamino group was much smaller than that of the vicinal substituent. The marked lability of the sulfoamino group in 2-deoxy-2-sulfoamino- D-glucose seems to be due to the overlapping of the multiple effects of hydroxyl groups, pyranose ring structure, and cyclic oxygen atom. Based on the liberation of amino and inorganic sulfate groups from amino alcohol sulfoamino groups, the possibility of trans-sulfation from N to O under the experimental conditions used is discussed.