Novel photoreactive cinnamic acid analogues to elucidate phenylalanine ammonia-lyase.
4-[3-(Trifluoromethyl) diazirinyl] cinnamic acid derivatives were synthesized to elucidate properties of phenylalanine ammonia-lyase (PAL). 2-Methoxy and 2-biotinylated alkoxy compounds have inhibitory activity on the formation of phenylalanine from cinnamic acid. Specific photolabeling of the enzyme was detected using biotinylated derivatives without the use of radioisotopes. The results indicated that the 4-[3-(trifluoromethyl) diazirinyl] skeleton will be a suitable photoreactive compound to elucidate regulation of phenylpropanoid biosynthesis.
Hashimoto
M
M
Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine, Hokkaido, Japan. hasimoto@obihiro.ac.jp
Hatanaka
Y
Y
Nabeta
K
K
D002934:Cinnamates / Q000737:chemistry*; D004591:Electrophoresis, Polyacrylamide Gel; D007700:Kinetics; D015394:Molecular Structure; D010649:Phenylalanine / Q000378:metabolism*; D010650:Phenylalanine Ammonia-Lyase / Q000037:antagonists & inhibitors / Q000378:metabolism*; D019920:Photoaffinity Labels / Q000138:chemical synthesis* / Q000378:metabolism; D012248:Rhodotorula / Q000201:enzymology
D002934:Cinnamates; D019920:Photoaffinity Labels; C029010:cinnamic acid; D010649:Phenylalanine; D010650:Phenylalanine Ammonia-Lyase