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...

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Veröffentlicht in:	Journal of medicinal chemistry 1982-04, Vol.25 (4), p.397-402
Hauptverfasser:	Kawai, M, Nyfeler, R, Berman, J M, Goodman, M
Format:	Artikel
Sprache:	eng
Schlagworte:	Anilides - chemical synthesis Anilides - pharmacology Aspartic Acid - analogs & derivatives Aspartic Acid - chemical synthesis Aspartic Acid - pharmacology Chemical Phenomena Chemistry Dipeptides - chemical synthesis Dipeptides - pharmacology Humans Molecular Conformation Structure-Activity Relationship Sweetening Agents - chemical synthesis
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Zusammenfassung:	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.
ISSN:	0022-2623
DOI:	10.1021/jm00346a013