title: Conformational flexibility of aspartame.
abstract: L-Aspartyl-L-phenylalanine methyl ester, better known as aspartame, is not only one of the most used artificial sweeteners, but also a very interesting molecule with respect to the correlation between molecular structure and taste. The extreme conformational flexibility of this dipeptide posed a huge difficulty when researchers tried to use it as a lead compound to design new sweeteners. In particular, it was difficult to take advantage of its molecular model as a mold to infer the shape of the, then unknown, active site of the sweet taste receptor. Here, we follow the story of the 3D structural aspects of aspartame from early conformational studies to recent docking into homology models of the receptor. © 2016 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 106: 376-384, 2016.
authors.affiliation: Department of Chemistry, University of Padova, Padova, Italy.
authors.forename: Claudio
authors.initials: C
authors.lastname: Toniolo
authors.affiliation: Department of Chemical Sciences, University of Naples, Naples, Italy.|Department of Basic and Clinical Neurosciences, University of London, Kings College London, London, United Kingdom.
authors.forename: Pierandrea
authors.initials: P
authors.lastname: Temussi
mesh_terms: D001218:Aspartame / Q000737:chemistry* / Q000378:metabolism; D001665:Binding Sites; D006801:Humans; D008968:Molecular Conformation; D062105:Molecular Docking Simulation; D011485:Protein Binding; D020033:Protein Isoforms / Q000737:chemistry / Q000378:metabolism; D055503:Protein Multimerization; D043562:Receptors, G-Protein-Coupled / Q000737:chemistry* / Q000378:metabolism; D013329:Structure-Activity Relationship; D013549:Sweetening Agents / Q000737:chemistry* / Q000378:metabolism; D013649:Taste / Q000502:physiology*
chemical_list: D020033:Protein Isoforms; D043562:Receptors, G-Protein-Coupled; D013549:Sweetening Agents; C431926:taste receptors, type 1; D001218:Aspartame
keywords: aspartame; molecular recognition; structure; sweet receptor; sweetener