二氢青蒿醛与贝蒂碱的结晶诱导非对映异构体转化
Crystallization-Induced Diastereoisomer Transformation of Dihydroartemisinic Aldehyde with the Betti Base.
作者信息
Zanetti Andrea, Chaumont-Olive Pauline, Schwertz Geoffrey, Nascimento de Oliveira Marllon, Gomez Fernandez Mario Andrés, Amara Zacharias, Cossy Janine
机构信息
Molecular, Macromolecular Chemistry and Materials, ESPCI Paris/CNRS/PSL Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
Equipe Chimie Moléculaire, Laboratoire de Génomique, Bioinformatique et Chimie Moléculaire (GBCM), EA 7528, Conservatoire national des arts et métiers, HESAM Université, 2 rue Conté, 75003 Paris Cedex 03, France.
出版信息
Org Process Res Dev. 2020 May 15;24(5):850-855. doi: 10.1021/acs.oprd.9b00481. Epub 2020 Jan 14.
Artemisinin is an important drug to fight malaria. It is produced either by extraction or via a semisynthetic route involving enzyme engineering. A key intermediate to produce artemisinin by the enzymatic route is dihydroartemisinic aldehyde (). However, control of the absolute configuration of the stereocenter α to the aldehyde is highly challenging. Herein we report a protocol that allows the diastereomeric enrichment of a mixture of (11)/(11)- to the desired (11)- by utilizing a crystallization-induced diastereomer transformation induced by the Betti base. In addition, the Betti base can be quantitatively recovered and reused after the reaction.
青蒿素是一种对抗疟疾的重要药物。它可以通过提取或通过涉及酶工程的半合成路线来生产。通过酶促路线生产青蒿素的关键中间体是二氢青蒿醛（）。然而，控制醛基α位立体中心的绝对构型极具挑战性。在此，我们报告了一种方案，该方案利用贝蒂碱诱导的结晶诱导非对映体转化，将（11）/（11）混合物非对映体富集为所需的（11）。此外，反应后贝蒂碱可以定量回收并重复使用。
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