HIGH-POTENCY DIPEPTIDE SWEETENERS .2. L-ASPARTYLFURYLGLYCINE THIENYLGLYCINE AND IMIDAZOLYLGLYCINE ESTERS

Eight L-aspartyl dipeptides derived from heterocyclic glycine esters were prepared and evaluated as sweeteners. The fenchyl esters of L-asparty1-2-furyl- 2- and 3-thienyl-, and imidazolylglycine were all potently sweet with the D-2-furylglycine (+)-β-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 β-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. © 1990, American Chemical Society. All rights reserved.