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 >90% correct. To elicit a sweet taste, the R group of the sulfamate should have x ≥ 5.2 Å and ≤ 7.2 Å and V (i.e., xyz) ≥250 ųand probably ≥90 ų. 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.