Synthesis of tag introducible (3-trifluoromethyl)phenyldiazirine based photoreactive phenylalanine.
An efficient synthesis of tag introducible (3-trifluoromethyl)phenyldiazirine based phenylalanine derivatives is described. Alkylation of a chiral glycine equivalent with a spacer containing (3-trifluoromethyl)phenyldiazirinyl bromides enables us to create photoreactive L-phenylalanine derivatives. After introduction of biotin at the spacer, the biotinylated and photoreactive amino acid was applied for L-amino acid oxidase and incorporated into a substrate binding site. These compounds will be powerful tools not only for photoaffinity labeling to elucidate properties of bioactive peptides but also as trifunctional photophors to introduce a ligand skeleton.
Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine, Inada-cho, Obihiro 080-8555, Hokkaido, Japan. hasimoto@obihiro.ac.jp
Makoto
M
Hashimoto
Yasumaru
Y
Hatanaka
Yutaka
Y
Sadakane
Kensuke
K
Nabeta
D001389:Azirines / Q000737:chemistry*; D001710:Biotin / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D010649:Phenylalanine / Q000138:chemical synthesis* / Q000737:chemistry; D019920:Photoaffinity Labels
C024282:3-trifluoromethyl-3-phenyldiazirine; D001389:Azirines; D019920:Photoaffinity Labels; D010649:Phenylalanine; D001710:Biotin