High potency dipeptide sweeteners. 1. L-aspartyl-D-phenylglycine esters.
Twenty esters of L-aspartyl-D-phenylglycine, as well as two substituted analogues, an o-fluoro and a p-hydroxy-phenylglycine ester, were prepared. The L-aspartyl-D-phenylglycine (-)-alpha- and (+)-beta-fenchyl esters had the highest sweetness potency at 1200 and 3700 times that of sucrose, respectively. The high potency of these sweeteners is surprising as the phenyl group occupies a position previously believed to accommodate only much smaller groups.
Janusz
J M
JM
Procter & Gamble Company, Miami Valley Laboratories, Cincinnati, Ohio 45239-8707.
Gardlik
J M
JM
Young
P A
PA
Burkes
R V
RV
Stoll
S J
SJ
Estelle
A F
AF
Riley
C M
CM
D000818:Animals; D001224:Aspartic Acid; D004151:Dipeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D004952:Esters; D005998:Glycine / Q000031:analogs & derivatives; D006801:Humans; D008297:Male; D051381:Rats; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013549:Sweetening Agents / Q000138:chemical synthesis* / Q000494:pharmacology
D004151:Dipeptides; D004952:Esters; D013549:Sweetening Agents; D001224:Aspartic Acid; C021316:N-phenylglycine; D005998:Glycine