4.5 Article

Promiscuous enzyme-catalyzed cascade reaction in water: Synthesis of dicoumarol derivatives

Journal

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 29, Issue 10, Pages 1236-1240

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2019.03.007

Keywords

Enzymatic synthesis; Cascade reactions; Aromatic aldehyde; 4-hydroxycoumarin; Dicoumarol derivatives

Funding

  1. National Natural Science Foundation of China [21676143]
  2. key laboratory of Materials-Oriented Chemical Engineering [ZK201603]
  3. Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture
  4. Qing Lan Project of Jiangsu Province

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Lipase RMIM was firstly used as a promiscuous biocatalyst to catalyze the Knoevenagel-Michael cascade reactions of 4-hydroxycoumarin with aromatic, heterocyclic or aliphatic aldehydes to synthesize dicoumarol derivatives in water. Results showed that the adopted methodology could offer many advantages, such as mild reaction conditions, pure aqueous reaction system, wide substrate applicability, recyclable catalyst, excellent yields (81-98%), operational simplicity, and environmentally friendly reactions.

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