Correlation Study on Sweetness of Amino Acid with Different Configurations and Quantum Chemical Parameters

1 INTRODUCTION Since the introduction of QSAR by Hansch and Fujita in 1964, Deutsch and Hansch have quickly used it in the study of nitrophenylamine sweet reagents. They found good correlation between their distribution coefficients in octanol/water system and sweetness degree. Subsequently, they detected that vibration of aroma-substituent compounds has so- mething to do with sweetness. Henceforth, statistic correlations between structure and sweetness ofseries compounds have been inv…

Correlation Study on Sweetness of Amino Acid with Different Configurations and Quantum Chemical Parameters

Quantum chemical parameters of 10 amino acids with D- and L-configurations were firstly calculated with semi-empirical AM1 method. Furthermore, the relationship between mole- cular structures of D-, L-amino acids and their sweetness were observed. The results show that upon different configurations of amino acids, the sweetness is relative with their formation heat, dipole moment, energy gap of frontier orbital and other parameters. The formation heats of the same amino acids possessing D- and L-configurations are different except glycine. The algebraic value of D- amino acid is generally larger than that of corresponding L-configuration with only one except of tyrosine. The dipole moment of D-amino acid is generally larger than that of corresponding L-amino acid except tyrosine and lysine. The lowest unoccupied orbital energy (ELUMO) of D-amino acid is higher than that of corresponding L-configuration except phenylalanine. △E of D-amino acid is larger than that of L-amino acid except histidine, phenylalanine and lysine. The larger gap will have advantage for its matching with frontier orbital energy of human protein acceptor, which strengthens the interaction between D-amino acid and sweet taste acceptor. Besides, the changing rules of these parameters are generally identical.