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Structure-activity studies on sulfamate sweeteners

G A Benson, W J Spillane

    Journal of Medicinal Chemistry
    |July 1, 1976
    PubMed
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    Researchers explored sulfamate sweeteners, synthesizing fifteen compounds to test structural limits for sweetness. They propose the CHN(R)SO3- group is essential for sweet taste, identifying the sulfamate SO3- group as the key sweetness receptor.

    Area of Science:

    • Organic Chemistry
    • Sweetener Chemistry
    • Structure-Activity Relationships

    Background:

    • Sulfamate compounds are known for their sweet taste.
    • Understanding the structural requirements for sweetness is crucial for designing new sweeteners.
    • Existing theories of sweetness, like the Shallenberger A-H,B theory, provide a framework for investigation.

    Purpose of the Study:

    • To review and elucidate the structure-activity relationships of sulfamate sweeteners.
    • To synthesize novel sulfamate compounds and evaluate their sweetness.
    • To determine the essential structural features required for a sulfamate to elicit a sweet taste.

    Main Methods:

    • Systematic review of structure-activity relationships based on chemical modifications.

    Related Experiment Videos

  • Synthesis of fifteen new sulfamate compounds.
  • Sensory evaluation of sweetness, including determination of threshold levels and relative sweetness for seven compounds.

    • Main Results:

    • Fifteen sulfamate compounds were synthesized to probe structural limitations without losing sweetness.
    • The grouping CHN(R)SO3- was identified as a necessary, though not sufficient, condition for sweetness.
    • The sulfamate SO3- group is proposed as the B-center in the Shallenberger A-H,B sweetness theory, rather than SO2-.

    Conclusions:

    • The specific arrangement of atoms within the sulfamate structure is critical for sweetness perception.
    • The SO3- group plays a pivotal role in the sweet taste mechanism of sulfamates.
    • Further research can be guided by these findings to develop novel, safe, and effective sweetening agents.