title: Photoactive ligands probing the sweet taste receptor. Design and synthesis of highly potent diazirinyl D-phenylalanine derivatives.
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.
authors.affiliation: Suntory Institute for Bioorganic Research, 1-1-1 Wakayamadai, Shimamoto-cho, Mishima-gun, Osaka 618-8503, Japan.
authors.forename: Katsuyoshi
authors.initials: K
authors.lastname: Masuda
authors.forename: Ayako
authors.initials: A
authors.lastname: Koizumi
authors.forename: Takumi
authors.initials: T
authors.lastname: Misaka
authors.forename: Yasumaru
authors.initials: Y
authors.lastname: Hatanaka
authors.forename: Keiko
authors.initials: K
authors.lastname: Abe
authors.forename: Takaharu
authors.initials: T
authors.lastname: Tanaka
authors.forename: Masaji
authors.initials: M
authors.lastname: Ishiguro
authors.forename: Makoto
authors.initials: M
authors.lastname: Hashimoto
mesh_terms: D002460:Cell Line; D018360:Crystallography, X-Ray; D006801:Humans; D010649:Phenylalanine / Q000138:chemical synthesis* / Q000378:metabolism*; D019920:Photoaffinity Labels / Q000138:chemical synthesis* / Q000378:metabolism*; D017434:Protein Structure, Tertiary; D043562:Receptors, G-Protein-Coupled / Q000737:chemistry / Q000378:metabolism*; D013549:Sweetening Agents / Q000378:metabolism; D013650:Taste Buds / Q000737:chemistry / Q000378:metabolism*
chemical_list: D019920:Photoaffinity Labels; D043562:Receptors, G-Protein-Coupled; D013549:Sweetening Agents; C431926:taste receptors, type 1; D010649:Phenylalanine