Structure-activity studies on sulfamate sweeteners

Abstract

The structure-activity relationships governing sulfamate sweeteners are reviewed under the headings: size of the reduced ring, changes in the sulfamate function, substitution of hydrogen in the ring, and substitution of carbon in the ring and open-chain compounds. Fifteen compounds have been synthesized with a view to testing the limitations on structural changes which may be made within these categories without loss of sweetness. The presence of the grouping > CHN(R)SO3- is suggested as a necessary but not a sufficient condition for a compound to be sweet-tasting. Thus, the B center of the Shallenberger A-H,B theory of sweetness is best regarded as being -SO3- rather than -SO2- for sulfamates. Threshold levels and relative sweetness have been determined for seven sulfamates.