title: Active conformations of neotame and other high-potency sweeteners.
abstract: We carried out extensive conformational analysis of three high-potency sweeteners: neotame, superaspartame, and SC-45647. We then identified six possible pharmacophore features (carboxylate, two hydrophobic groups, and three NH groups) and wrote a computer program to exhaustively compare intramolecular distances among all possible sets of five-point pharmacophores (carboxylate + two hydrophobic groups + two NH groups) for the three compounds. The best pharmacophore model superimposes low-energy conformers of the three compounds in such a way that the five pharmacophore points match well both sterically and with respect to orientation of hydrogen bond donors and acceptors.
authors.affiliation: Department of Biochemistry and Molecular Biology, Finch University of Health Sciences/The Chicago Medical School, 3333 Green Bay Road, North Chicago, Illinois 60064, USA. Eric.Walters@finchcms.edu
authors.forename: D E
authors.initials: DE
authors.lastname: Walters
authors.forename: I
authors.initials: I
authors.lastname: Prakash
authors.forename: N
authors.initials: N
authors.lastname: Desai
mesh_terms: D004151:Dipeptides / Q000737:chemistry*; D006146:Guanidines / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D012984:Software; D013549:Sweetening Agents / Q000737:chemistry*
chemical_list: D004151:Dipeptides; D006146:Guanidines; C099860:SC 45647; D013549:Sweetening Agents; C404525:neotame