Structure-activity studies on sulfamate sweeteners.
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 greater than 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.
D000588:Amines / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D013549:Sweetening Agents / Q000138:chemical synthesis*; D013652:Taste Threshold
D000588:Amines; D013451:Sulfonic Acids; D013549:Sweetening Agents; C005741:sulfamic acid