Enantioselective Oxidative Aerobic Dealkylation of N‐Ethyl Benzylisoquinolines by Employing the Berberine Bridge Enzyme |
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| Authors: | Somayyeh Gandomkar Eva‐Maria Fischereder Dr. Joerg H. Schrittwieser Dr. Silvia Wallner Dr. Zohreh Habibi Prof. Dr. Peter Macheroux Prof. Dr. Wolfgang Kroutil |
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| Affiliation: | 1. Institut für Chemie, Organische & Bioorganische Chemie, Universit?t Graz, NAWI Graz, Heinrichstra?e 28, 8010 Graz (Austria);2. Department of Pure Chemistry, Faculty of Chemistry, Shahid Beheshti University, G.C. District 1, Evin, Daneshjou Blvd, Tehran (Iran);3. Institut für Biochemie, Technische Universit?t Graz, Petersgasse 12, 8010 Graz (Austria) |
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| Abstract: | N‐Dealkylation methods are well described for organic chemistry and the reaction is known in nature and drug metabolism; however, to our knowledge, enantioselective N‐dealkylation has not been yet reported. In this study, exclusively the (S)‐enantiomers of racemic N‐ethyl tertiary amines (1‐benzyl‐N‐ethyl‐1,2,3,4‐tetrahydroisoquinolines) were dealkylated to give the corresponding secondary (S)‐amines in an enantioselective fashion at the expense of molecular oxygen. The reaction is catalyzed by the berberine bridge enzyme, which is known for C? C bond formation. The dealkylation was demonstrated on a 100 mg scale and gave optically pure dealkylated products (ee>99 %). |
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| Keywords: | alkaloids asymmetric synthesis enantioselective enzyme catalysis N‐dealkylation |
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