title: Exploring the biological consequences of conformational changes in aspartame models containing constrained analogues of phenylalanine.
abstract: The dipeptide aspartame (Asp-Phe-OMe) is a sweetener widely used in replacement of sucrose by food industry. 2',6'-Dimethyltyrosine (DMT) and 2',6'-dimethylphenylalanine (DMP) are two synthetic phenylalanine-constrained analogues, with a limited freedom in χ-space due to the presence of methyl groups in position 2',6' of the aromatic ring. These residues have shown to increase the activity of opioid peptides, such as endomorphins improving the binding to the opioid receptors. In this work, DMT and DMP have been synthesized following a diketopiperazine-mediated route and the corresponding aspartame derivatives (Asp-DMT-OMe and Asp-DMP-OMe) have been evaluated in vivo and in silico for their activity as synthetic sweeteners.
authors: a Dipartimento di Farmacia, Università di Chieti-Pescara "G. d'Annunzio" , Chieti , Italy .
authors: Adriano
authors: A
authors: Mollica
authors: b Department of Biochemistry, Sanandaj Branch , Islamic Azad University , Sanandaj , Iran .
authors: Sako
authors: S
authors: Mirzaie
authors: a Dipartimento di Farmacia, Università di Chieti-Pescara "G. d'Annunzio" , Chieti , Italy .
authors: Roberto
authors: R
authors: Costante
authors: a Dipartimento di Farmacia, Università di Chieti-Pescara "G. d'Annunzio" , Chieti , Italy .
authors: Simone
authors: S
authors: Carradori
authors: a Dipartimento di Farmacia, Università di Chieti-Pescara "G. d'Annunzio" , Chieti , Italy .
authors: Giorgia
authors: G
authors: Macedonio
authors: c Dipartimento di Chimica, Sapienza Università di Roma , Rome , Italy .
authors: Azzurra
authors: A
authors: Stefanucci
authors: d Institute of Biochemistry, Biological Research Centre, Hungarian Academy of Sciences , Temesvari krt , Hungary , and.
authors: Szabolcs
authors: S
authors: Dvoracsko
authors: e Dipartimento di Farmacia, Università di Napoli "Federico II" , Naples , Italy.
authors: Ettore
authors: E
authors: Novellino
mesh_terms: D001218:Aspartame / Q000031:analogs & derivatives* / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D008958:Models, Molecular; D008968:Molecular Conformation; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013549:Sweetening Agents / Q000737:chemistry*
chemical_list: D013549:Sweetening Agents; D010649:Phenylalanine; D001218:Aspartame
keywords: 2′; 6′-dimethylphenylalanine; 6′-dimethyltyrosine; Aspartame; T1R2 receptor; computational methods; sweetener