High-potency dipeptide sweeteners. 2. L-aspartylfuryl-, thienyl-, and imidazolylglycine esters.
Eight L-aspartyl dipeptides derived from heterocyclic glycine esters were prepared and evaluated as sweeteners. The fenchyl esters of L-aspartyl-2-furyl-, 2- and 3-thienyl-, and imidazolylglycine were all potently sweet with the D-2-furylglycine (+)-beta-fenchyl ester being the most potent at 16,500 times the potency of sucrose. The requirement for a planar heterocyclic group directly attached to the glycine carbon atom was demonstrated by the observation that the tetrahydrofuryl and beta-thienylalanine fenchyl esters were not sweet. The heteroaromatic glycine esters join the phenylglycine esters as a novel class of dipeptide sweeteners with very high potency.
Janusz
J M
JM
Procter & Gamble Company, Miami Valley Laboratories, Cincinnati, Ohio 45239-8707.
Young
P A
PA
Blum
R B
RB
Riley
C M
CM
D000818:Animals; D004151:Dipeptides / Q000138:chemical synthesis; D004952:Esters / Q000138:chemical synthesis / Q000494:pharmacology; D005663:Furans / Q000138:chemical synthesis; D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis; D008297:Male; D051381:Rats; D013549:Sweetening Agents / Q000138:chemical synthesis*; D013876:Thiophenes / Q000138:chemical synthesis
D004151:Dipeptides; D004952:Esters; D005663:Furans; D007093:Imidazoles; D013549:Sweetening Agents; D013876:Thiophenes