Biomimetic Chiral Pyridoxal and Pyridoxamine Catalysts
Biomimetic Chiral Pyridoxal and Pyridoxamine Catalysts
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仿生手性吡哆醛和吡哆胺催化剂
DOI：
10.1002/cjoc.201800478
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发表时间：
2019-02-01
影响因子：
5.4
通讯作者：
Zhao, Baoguo
中科院分区：
文献类型：
--
作者：
Chen, Jianfeng;Liu, Yong Ethan;Zhao, Baoguo
维生素B-6是生物系统中的通用辅酶。然而，它的催化能力还没有被应用到不对称催化领域。基于维生素B-6的核心结构，我们开发了几种不同结构骨架和不同电子性质的吡哆醛和吡哆胺催化剂。以这些吡哆醛和吡哆胺为催化剂，我们分别实现了α-酮酸的仿生不对称转氨基反应和甘氨酸的仿生不对称Mannich反应，以良好的产率和良好的手性选择性合成了多种手性α-氨基酸和α，β-二氨基酸。这两种反应都完美地模拟了相应的生物转化。
Vitamin B-6 serves as universal co-enzymes in biological systems. However, its catalytic power has not been applied into the area of asymmetric catalysis. Based on the core structure of vitamin B-6, we have developed several types of pyridoxal and pyridoxamine catalysts with different structural skeletons and different electronic properties. With these pyridoxals and pyridoxamines as catalysts, we have realized biomimetic asymmetric transamination of alpha-keto acids and biomimetic asymmetric Mannich reaction of glycinate, respectively, to give various chiral alpha-amino acids and alpha,beta-diamino acids in good yields with excellent diastero- and/or enantioselectivities. Both of the reactions have perfectly mimicked the corresponding biological transformations.