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Selective Hydrogenation of Alkene in (3-Trifluoromethyl) Phenyldiazirine Photophor with Wilkinson's Catalyst for Photoaffinity Labeling

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Title: Selective Hydrogenation of Alkene in (3-Trifluoromethyl) Phenyldiazirine Photophor with Wilkinson's Catalyst for Photoaffinity Labeling
Authors: Hashimoto, Makoto Browse this author →KAKEN DB
Kato, Yuh-hi Browse this author
Hatanaka, Yasumaru Browse this author
Keywords: photoaffinity labeling
Wilkinson's catalyst
Issue Date: Oct-2007
Publisher: Pharmaceutical Society of Japan
Journal Title: Chemical & pharmaceutical bulletin
Volume: 55
Issue: 10
Start Page: 1540
End Page: 1543
Abstract: Selective hydrogenation of carbon-carbon double bond in the presence of nitrogen-nitrogen double bond in (3-trifluoromethyl) phenyldiazirine achieved with Wilkinson's catalyst. Photoaffinity labeling is a powerful method in the study of biological structures and functions. 1, 2) It is suitable for the analysis of biological interactions because it is based on the affinity of the ligand moiety. Various photophors, such as phenyldiazirine, arylazide and benzophenone, were used. Comparative irradiation studies of these three photophors in living cells suggested that a carbene precursor, (3-trifluoromethyl) phenyldiazirine, is the most promising, 3-6) but complicated synthesis of the diazirinyl three-membered ring prevented the application of the photophor. Post-functional synthesis of TPD derivatives is one of problems to be solved. 7-10) It is well known that catalytic transfer hydrogenation followed by Wittig reaction is a useful method for general purpose carbon elongation, but the synthetic route does not apply for diazirinyl compounds, because it was reported that the diazirinyl nitrogen-nitrogen double bond was not tolerated under a hydrogen atmosphere in the presence of Pd-C for more than 1 h. 11, 12) Although the selective hydrogenation of alkene in diazirinyl and other photophors containing photo ligand in the presence of Pd/C was reported very recently, the hydrogenation of diazirinyl derivatives is low yield compared with other photophors due to the presence of the homogeneous N=N double bond. 13) Furthermore, the applications of the method were not reported.
Type: article
Appears in Collections:農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 橋本 誠

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