Stereoselective synthesis of (E)- and (Z)-beta-bromostyrene containing trifluoromethyldiazirine for photoaffinity labeling.
Summary A convenient procedure for the synthesis of (E)- and (Z)-beta-bromostyrene containing trifluoromethyldiazirine is described, which involves the stereoselective reduction of the corresponding trifluoromethyldiazirinyl beta,beta-dibromostyrene without damaging the photophor. The synthetic route easily introduced deuterium, which can be utilized for the detection of a photolabeled component by MS spectrometry, after construction of a trifluoromethyldiazirinyl skeleton.
Hashimoto
Makoto
M
Department of Agricultural and Life Science, Obihiro University of Agriculture and Veterinary Medicine, Obihiro Hokkaido, Japan. hasimoto@obihiro.ac.jp
Komano
Tomoko
T
Nabeta
Kensuke
K
Hatanaka
Yasumaru
Y
D003978:Diazomethane / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D019920:Photoaffinity Labels / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013343:Styrenes / Q000138:chemical synthesis*
D019920:Photoaffinity Labels; D013343:Styrenes; C018238:beta-bromostyrene; D003978:Diazomethane