Structure-activity studies on sulfamate sweeteners

J Med Chem. 1976 Jul;19(7):869-72. doi: 10.1021/jm00229a002.

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 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.

MeSH terms

  • Amines / chemical synthesis
  • Amines / pharmacology
  • Humans
  • Structure-Activity Relationship
  • Sulfonic Acids / chemical synthesis*
  • Sulfonic Acids / pharmacology
  • Sweetening Agents / chemical synthesis*
  • Taste Threshold

Substances

  • Amines
  • Sulfonic Acids
  • Sweetening Agents
  • sulfamic acid