The effect on taste upon the introduction of heteroatoms in sulphamates

The effect on taste of introducing a heteroatom(s) in place of a carbon atom(s) in sulphamate tastants has been examined in this work. Seventy sets of heterosulphamates and their corresponding carbon analogues (130 compounds in total) were examined. This interesting database was assembled by bringing together series of heterocompounds and suitable nonhetero analogues from the literature, by the synthesis in this work of 15 new heterosulphamates and two new carbosulphamates, which was necessary "to match up" with known carbosulphamate analogues and by making taste predictions for ten carbosulphamates which are unknown, using existing well-established structure-taste relationships (SARs). A sulphur atom replaced a carbon atom in 18 cases, either oxygen or an -OH group replaced carbon in 16 cases, and there are 29 examples where a nitrogen atom or an -NH group replaced carbon. Finally, there are six instances of a "double carbon-carbon, nitrogen-nitrogen substitution" and one of a treble carbon, nitrogen substitution. The overall picture shows that in 33 instances no change in taste was found when substitution occurred, in 29 instances sweet taste (S) was removed giving a nonsweet compound (N), and in eight instances a nonsweet material (N) became sweet (S). Replacement of oxygen by sulphur resulted in the introduction of sweetness in three cases out of four examined. Several important findings were made and a number of new structure-taste relationships have been derived for heterosulphamates.