A Facile Chemoenzymatic Approach: One‐Step Syntheses of Monoterpenoid Indole Alkaloids |
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Authors: | Dr Hong‐Bin Zou Hua‐Jian Zhu Liang Zhang Liu‐Qing Yang Prof?Dr Yong‐Ping Yu Prof?Dr Joachim Stöckigt |
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Institution: | 1. College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058 (China), Fax: (+86)?0571‐88208452, Fax: (+86)?0571‐88208449;2. Institut für Pharmazie und Biochemie, Johannes‐Gutenberg Universit?t Mainz, 55099 Mainz (Germany) |
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Abstract: | Facile chemoenzymatic syntheses of cytotoxic monoterpenoid indole alkaloids with novel skeletons and multiple chiral centers are described. Synthesis of these alkaloids was achieved by a simple one‐step reaction using strictosidine and 12‐aza‐strictosidine as the key intermediates. Strictosidines were prepared by coupling of secologanin with tryptamine and 7‐aza‐tryptamine, respectively, using the immobilized recombinant Rauvolfia strictosidine synthase. A detailed stereochemical analysis is presented herein. The results provide an opportunity for a chemoenzymatic approach that leads to an increased diversification of complex alkaloids with improved structures and activities. |
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Keywords: | alkaloids chemoenzymatic approach cytotoxicity indoles stereochemistry |
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