open access

https://hdl.handle.net/2115/64918

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

英語

Wilkinson's catalyst

2007-10

Pharmaceutical Society of Japan

Chemical & pharmaceutical bulletin

55(10)

1540-1543

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.

学術雑誌論文

Version of Record

0009-2363

1347-5223