Iwamura H
J Med Chem. 1981 May;24(5):572-83. doi: 10.1021/jm00137a018.
The relationship between structure and the sweet potency of L-aspartyl dipeptide analogues was investigated by physicochemical parameters and regression analysis. The dipeptide analogues reported were divided into the following four classes: L-aspartic acid amides, L-aspartylaminoethyl esters, L-aspartylaminopropionates, and L-aspartyl-aminoacetates. The analysis carried out for each class indicated that the electron-withdrawing effect of the substituents directed to the peptide bond and the steric dimensions of the molecules are important in eliciting the sweet taste. The values of coefficients of the electronic sigma terms in the correlations for L-aspartic acid amides, L-aspartylaminoethyl esters, and L-aspartylaminopropionates were approximately 0.7, indicating a common basic site on the receptor surface. The value for L-aspartylaminoacetates was approximately 1.5, and this value suggests, together with the factor of the participation of steric parameters, a closer or geometrically more proper fit to the receptor, explaining the generally higher potency of this class compared to the other three. The receptor model drawn based on these quantitative analyses appears to be consistent with other classes of sweeteners of apparently unrelated structures.
通过物理化学参数和回归分析研究了L-天冬氨酰二肽类似物的结构与甜味效力之间的关系。所报道的二肽类似物分为以下四类：L-天冬氨酸酰胺、L-天冬氨酰氨基乙酯、L-天冬氨酰氨基丙酸酯和L-天冬氨酰氨基乙酸酯。对每一类进行的分析表明，导向肽键的取代基的吸电子效应和分子的空间尺寸对引发甜味很重要。L-天冬氨酸酰胺、L-天冬氨酰氨基乙酯和L-天冬氨酰氨基丙酸酯相关性中电子σ项的系数值约为0.7，表明受体表面存在一个共同的碱性位点。L-天冬氨酰氨基乙酸酯的值约为1.5，这个值与空间参数参与的因素一起表明与受体的结合更紧密或在几何形状上更合适，这解释了该类化合物通常比其他三类具有更高的效力。基于这些定量分析绘制的受体模型似乎与其他结构明显无关的甜味剂类别一致。
