Conformational analysis of the dipeptide taste ligand L-aspartyl-D-2-aminobutyric acid-(S)-alpha-ethylbenzylamide and its analogues by NMR spectroscopy, computer simulations and X-ray diffraction studies.
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.
Goodman
M
M
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla 92093-0343, USA.
Zhu
Q
Q
Kent
D R
DR
Amino
Y
Y
Iacovino
R
R
Benedetti
E
E
Santini
A
A
D000613:Aminobutyrates / Q000138:chemical synthesis* / Q000737:chemistry; D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D003198:Computer Simulation; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008958:Models, Molecular; D011487:Protein Conformation; D013549:Sweetening Agents / Q000138:chemical synthesis* / Q000737:chemistry
D000613:Aminobutyrates; D013549:Sweetening Agents; C108973:aspartyl-2-aminobutyric acid ethylbenzylamide; D001224:Aspartic Acid