Cytochrome P450-Catalyzed O-Dealkylation.pdfVIP

A RTICLE Cytochrome P450-Catalyzed O-Dealkylation Coupled With Photochemical NADPH Regeneration Sahng Ha Lee,1 Yong-Chan Kwon,2 Dong-Myung Kim,2 Chan Beum Park1 1 Department of Materials Science and Engineering, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 305-701, Korea; telephone: þ82-42-350-3340; fax: þ82-42-350-331; e-mail: parkcb@kaist.ac.kr 2 Department of Fine Chemical Engineering and Applied Chemistry, Chungnam National University, Daejeon 305-764, Korea; telephone: þ82-42-821-5899; fax: þ82-42-822-6637; e-mail: dmkim@cnu.ac.kr Introduction ABSTRACT: Cytochrome P450 monooxygenases are multi- functional enzymes with potential applications in chemoen- Cytochrome P450 is a family of heme-containing mono- zymatic synthesis of complex chemicals as well as in studies oxygenases that can catalyze various regioselective and of metabolism and xenobiotics. Widespread application of stereospecific oxygen insertion reactions, such as aromatic cytochrome P450s, however, is encumbered by the critical amine oxidation, deamination, hydroxylation, and deal- need for redox equivalents in their catalytic function. To overcome this limitation, we studied visible light-driven kylation (Meunier et al., 2004). Due to these unique catalytic regeneration of NADPH for P450-catalyzed O-dealkylation properties, enormous efforts had been made to apply reaction; we used eosin Y as a photosensitizing dye, trietha- P450s in various complex synthetic reactions (Meunier nolamine as an electron donor, and [CpRh(bpy)H O] as an 2 et al.,