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Note | Special issue | Vol 82, No. 1, 2010, pp.909-915
Published online, 22nd July, 2010
DOI: 10.3987/COM-10-S(E)57
Simple Deuterium Introduction at α-Position of Carbonyl in Diazirinyl Derivatives for Photoaffinity Labeling

Yuta Murai, Miho Takahashi, Yasuyuki Muto, Yasumaru Hatanaka, and Makoto Hashimoto*

*Graduate School of Agriculture, Hokkaido University, Kita 9 Nishi 9, Kita-ku, Sapporo, Hokkaido 060-0589, Japan

Abstract

Post-functional deuterium incorporation into diazirinyl acetophenone derivatives is reported. Treatment of the compounds with sodium hydroxide in CH3OD at rt for 10 min achieved deuterium incorporation at α-position of the carbonyl group without decomposition of diazirinyl ring. Further deuterium can introduce by reduction of benzyl carbonyl with triethylsilane-d-TFA. Straightforward deuterium introduction into diazirinyl derivatives may contribute to the functional analysis of low molecular compounds with diazirine-based photoaffinity labeling.