Peptide sweeteners. 5. Side-chain homologues relating zwitterionic and trifluoroacetylated amino acid anilide and dipeptide sweeteners.
Side-chain homologues of sweet trifluoroacetyl-alpha-L-aspartyl-p-cyanoanilide have been synthesized and tasted. Removal of the trifluoroacetyl group only changes the potency of sweet taste, not the taste property. These results have been compared with the structure-taste relationships of dipeptide sweeteners. An informative discontinuity of taste effects was found to exist with novel aminomalonyl dipeptide derivatives. The results are explained on topochemical grounds.
D000813:Anilides / Q000138:chemical synthesis / Q000494:pharmacology; D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D004151:Dipeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D008968:Molecular Conformation; D013329:Structure-Activity Relationship; D013549:Sweetening Agents / Q000138:chemical synthesis*
D000813:Anilides; D004151:Dipeptides; D013549:Sweetening Agents; D001224:Aspartic Acid