Photoactive ligands probing the sweet taste receptor. Design and synthesis of highly potent diazirinyl D-phenylalanine derivatives.
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.
Masuda
Katsuyoshi
K
Suntory Institute for Bioorganic Research, 1-1-1 Wakayamadai, Shimamoto-cho, Mishima-gun, Osaka 618-8503, Japan.
Koizumi
Ayako
A
Misaka
Takumi
T
Hatanaka
Yasumaru
Y
Abe
Keiko
K
Tanaka
Takaharu
T
Ishiguro
Masaji
M
Hashimoto
Makoto
M
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*
D019920:Photoaffinity Labels; D043562:Receptors, G-Protein-Coupled; D013549:Sweetening Agents; C431926:taste receptors, type 1; D010649:Phenylalanine