Structure-activity studies on sulfamate sweeteners. 1976

G A Benson, and W J Spillane

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.

UI MeSH Term Description Entries
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000588 Amines A group of compounds derived from ammonia by substituting organic radicals for the hydrogens. (From Grant & Hackh's Chemical Dictionary, 5th ed) Amine
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013451 Sulfonic Acids Inorganic or organic oxy acids of sulfur which contain the RSO2(OH) radical. Sulfonic Acid,Acid, Sulfonic,Acids, Sulfonic
D013549 Sweetening Agents Substances that sweeten food, beverages, medications, etc., such as sugar, saccharine or other low-calorie synthetic products. (From Random House Unabridged Dictionary, 2d ed) Artificial Sweeteners,Sugar Substitutes,Sweeteners,Agent, Sweetening,Agents, Sweetening,Artificial Sweetener,Substitute, Sugar,Substitutes, Sugar,Sugar Substitute,Sweetener,Sweetener, Artificial,Sweeteners, Artificial,Sweetening Agent
D013652 Taste Threshold The minimum concentration at which taste sensitivity to a particular substance or food can be perceived. Taste Thresholds,Threshold, Taste,Thresholds, Taste

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