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Photoactive ligands probing the sweet taste receptor. Design and synthesis of highly potent diazirinyl d-phenylalanine derivatives
Authors:Katsuyoshi Masuda  Ayako Koizumi  Takumi Misaka  Yasumaru Hatanaka  Keiko Abe  Takaharu Tanaka  Masaji Ishiguro  Makoto Hashimoto
Institution:1. Suntory Institute for Bioorganic Research, 1-1-1 Wakayamadai, Shimamoto-cho, Mishima-gun, Osaka 618-8503, Japan;2. Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan;3. Faculty of Pharmaceutical Sciences, Toyama University, 2360 Sugitani, Toyama 930-0194, Japan;4. Division of Applied Science, Graduate School of Agriculture, Hokkaido University, Kita 9, Nishi 9, Kita-ku, Sapporo 060-8589, Japan
Abstract:Some d-Amino acids such as d-tryptophan and d-phenylalanine are well known as naturally-occurring sweeteners. Photoreactive d-phenylalanine derivatives containing trifluoromethyldiazirinyl moiety at 3- or 4-position of phenylalanine, were designed as sweeteners for functional analysis with photoaffinity labeling. The trifluoromethyldiazirinyl d-phenylalanine derivatives were prepared effectively with chemo-enzymatic methods using l-amino acid oxidase and were found to have potent activity toward the human sweet taste receptor.
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