A facile chemoenzymatic approach: one-step syntheses of monoterpenoid indole alkaloids
Hong-Bin Zou1, Hua-Jian Zhu, Liang Zhang
1College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China.
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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