Structure-activity studies on sulfamate sweeteners II: semiquantitative structure-taste relationship for sulfamate (RNHSO-3) sweeteners-the role of R.
With the use of Corey-Pauling -Koltun space-filling models, measurements of defined parameters (x, y, and z) were made of the R groups in a large number of carbosulfamates, RNHSO-3. The correlation between sweet and nonsweet sulfamates and the defined parameters for R is good. As a test, 12 new carbosulfamates were synthesized and tasted. The predictions of their sweetness or nonsweetness based on the correlation were greater than 90% correct. To elicit a sweet taste, the R group of the sulfamate should have x greater than or equal to 5.2 A and less than or equal to 7.2 A and V (i.e.,xyz) less than or equal to 250 A3 and probably greater than or equal to 90 A3. The receptor site is seen (as for aspartame) as a rather narrow cleft into which R has to fit "properly" or be "locked" so that the AH,B mechanism for initiating the sweet stimulae can operate. Possible applications of this approach are indicated.
D006801:Humans; D008962:Models, Theoretical; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids; D013549:Sweetening Agents; D013649:Taste
D013451:Sulfonic Acids; D013549:Sweetening Agents; C005741:sulfamic acid