Cyclopropane amino acid ester dipeptide sweeteners.
A series of esters of L-aspartyl-1-aminocyclopropane carboxylic acid has been prepared and their sweet tastes determined. The sweetest ester prepared was about 300 times sweeter than sucrose. An attempt to use basic conditions during preparation of the dipeptide allyl ester led to succinimide formation of the aspartyl peptide even though the beta-carboxyl group was protected by a t-butyl ester function. The X-ray structure of the propyl ester (1c) was determined and its conformation is discussed.
Department of Chemistry, School of Chemical Sciences, University of Georgia, Athens.
C
C
Mapelli
M G
MG
Newton
C E
CE
Ringold
C H
CH
Stammer
D001218:Aspartame / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D004151:Dipeptides / Q000138:chemical synthesis*; D004952:Esters; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009904:Optical Rotation; D011487:Protein Conformation; D013329:Structure-Activity Relationship; D013549:Sweetening Agents / Q000138:chemical synthesis*; D013649:Taste; D014961:X-Ray Diffraction
D004151:Dipeptides; D004952:Esters; D013549:Sweetening Agents; D001218:Aspartame