Journal
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
Volume 31, Issue 6, Pages 953-963Publisher
TAYLOR & FRANCIS LTD
DOI: 10.3109/14756366.2015.1076811
Keywords
Aspartame; computational methods; 2 ',6 '-dimethyltyrosine; 2 ',6 '-dimethylphenylalanine; sweetener; T1R2 receptor
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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 chi-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.
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