College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China.
Chem Asian J. 2010 Nov 2;5(11):2400-4. doi: 10.1002/asia.201000520.
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.
描述了具有新型骨架和多个手性中心的细胞毒性单萜吲哚生物碱的简便化学生酶合成。这些生物碱的合成是通过使用育亨宾和 12-氮杂育亨宾作为关键中间体的简单一步反应实现的。使用固定化重组萝芙木育亨宾合酶，分别将卫矛醇与色胺和 7-氮杂色胺偶联，制备了育亨宾。本文提出了详细的立体化学分析。这些结果为化学生酶方法提供了机会，从而可以增加结构和活性得到改善的复杂生物碱的多样化。
