ChemInform Abstract: Simple Deuterium Introduction at α‐Position of Carbonyl in Diazirinyl Derivatives for Photoaffinity Labeling.

Abstract

Simple Deuterium Introduction at α-Position of Carbonyl in Diazirinyl Derivatives for Photoaffinity Labeling. -Deuterium incorporation into diazirinyl acetophenone derivative (I) proceeds at the α-position of the carbonyl group without decomposition of the diazirinyl ring. Additional deuterium can be introduced by reduction of the benzyl carbonyl and subsequent treatment with triethylsilane-D-TFA. Similarly, subjecting diazirinyl fatty acid derivative (V) to H/D exchange reactions proceeds in a selective fashion. Methyl ester (VII) is hydrolyzed without loss of deuterium. -(MURAI, Y.; TAKAHASHI, M.; MUTO, Y.; HATANAKA, Y.; HASHIMOTO*, M.; Heterocycles 82 (2010) 1, 909-915, http://dx.doi.org/10.3987/com-10-s(e)57 ; Grad. Sch. Agric., Hokkaido Univ., Kita, Sapporo 060, Japan; Eng.) -H. Hoennerscheid

Selective Hydrogenation and Transfer Hydrogenation for Post-Functional Synthesis of Trifluoromethylphenyl Diazirine Derivatives for Photoaffinity Labeling

“…These synthetic methodologies have also been applied to synthesis of deuterium incorporated photoreactive fatty acid derivatives. (Murai et al 2010) …”