Goodman M, Zhu Q, Kent D R, Amino Y, Iacovino R, Benedetti E, Santini A
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla 92093-0343, USA.
J Pept Sci. 1997 May-Jun;3(3):231-41. doi: 10.1002/(sici)1099-1387(199705)3:3<231::aid-psc105>3.0.co;2-3.
A dipeptide taste ligand L-aspartyl-D-2-aminobutyric acid-(S)-alpha-ethylbenzylamide was found to be about 2000 times more potent than sucrose. To investigate the molecular basis of its potent sweet taste, we carried out conformational analysis of this molecular and several related analogues by NMR spectroscopy, computer simulations and X-ray crystallographic studies. The results of the studies support our earlier model that an L-shape molecular array is essential for eliciting sweet taste. In addition, we have identified an aromatic group located between the stem and the base of the L-shape, which is responsible for enhancement of sweetness potency. In this study, we also assessed the optimal size of the essential hydrophobic group (X) and the effects of the chirality of the second residue toward taste.
发现一种二肽味觉配体L-天冬氨酰-D-2-氨基丁酸-(S)-α-乙基苄基酰胺的甜度约为蔗糖的2000倍。为了研究其强烈甜味的分子基础，我们通过核磁共振光谱、计算机模拟和X射线晶体学研究对该分子及几种相关类似物进行了构象分析。研究结果支持了我们早期的模型，即L形分子阵列是引发甜味所必需的。此外，我们还确定了一个位于L形分子的茎和基部之间的芳香基团，它负责增强甜味强度。在本研究中，我们还评估了必需疏水基团(X)的最佳大小以及第二个残基的手性对味觉的影响。
