Synthesis and sweetness characteristics of L-aspartyl-D-alanine fenchyl esters.
Four isomers of the L-aspartyl-D-alanine fenchyl esters were prepared as potential peptide sweeteners. L-Aspartyl-D-alanine (+)-alpha-fenchyl ester and L-aspartyl-D-alanine (-)-beta-fenchyl ester showed sweetness with potencies 250 and 160 times higher than that of sucrose, respectively. In contrast, L-aspartyl-D-alanine (+)-beta-fenchyl ester and L-aspartyl-D-alanine (-)-alpha-fenchyl ester had the highest sweetness potencies at 5700 and 1100 times that of sucrose, respectively. In particular, L-aspartyl-D-alanine (-)-alpha-fenchyl ester had an excellent sweetness quality; but L-aspartyl-D-alanine (+)-beta-fenchyl ester did not have an excellent quality of sweetness because it displayed an aftertaste caused by the strong sweetness.
Yuasa
Y
Y
Technical and Engineering Department, Fine Chemical Division, Takasago International Corporation, 1-5-1 Nishiyawata, Hiratsuka, Kanagawa, 254-0073, Japan. TIC00488@nifty.ne.jp
Nagakura
A
A
Tsuruta
H
H
D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009636:Norbornanes / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D020033:Protein Isoforms; D013395:Sucrose; D013549:Sweetening Agents / Q000138:chemical synthesis* / Q000737:chemistry; D013649:Taste
D004151:Dipeptides; D009636:Norbornanes; D020033:Protein Isoforms; D013549:Sweetening Agents; C439409:aspartyl-alanine fenchyl ester; D013395:Sucrose