Molecular basis of sweet taste in dipeptide taste ligands

Goodman, M.; Valle, J. R. Del; Amino, Y.; Benedetti, E.

doi:10.1351/pac200274071109

Pure Appl. Chem., 2002, Vol. 74, No. 7, pp. 1109-1116

http://dx.doi.org/10.1351/pac200274071109

Molecular basis of sweet taste in dipeptide taste ligands

M. Goodman¹*, J. R. Del Valle¹, Y. Amino² and E. Benedetti³

¹ Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093-0343, USA
² Ajinomoto Co., Inc., AminoScience Laboratories, 1-1 Suzuki-Cho, Kawasaki-Ku, Kawasaki-Shi 210-8681, Japan
³ Center of Biocrystallography, University of Naples, Via Mezzocannone 6, Naples, Italy

Abstract: In this presentation, we describe an integrated approach for the molecular basis for sweet taste among dipeptide-based ligands. By comparing the results obtained from X-ray diffraction studies with the conformations from NMR analysis and molecular modeling, we have observed recurring topochemical motifs that agree with previous models for sweet taste. In our examination of the unexplored D zone of the TintiNofre model, we have uncovered a sweet potency enhancing effect of a new set of aralkyl-substitutions on dipeptide ligands, which reveals the importance of aromaticaromatic interactions in maintaining high potency.