Enzyme-Inspired Axially Chiral Pyridoxamines Armed with a Cooperative Lateral Amine Chain for Enantioselective Biomimetic Transamination

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• 作者：Yong Ethan Liu ; Zhaole Lu ; Bo Li ; Jiaxin Tian ; Feng Liu ; Junyu Zhao ; Chengkang Hou ; Yingkun Li ; Lili Niu ; Baoguo Zhao
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：August 31, 2016
• 年：2016
• 卷：138
• 期：34
• 页码：10730-10733
• 全文大小：405K
• 年卷期：0
• ISSN：1520-5126

文摘

Enzymatic transamination is catalyzed by pyridoxal/pyridoxamine, and it involves remarkable cooperative catalysis of a Lys residue in the transaminase. Inspired by transaminases, we developed a class of axially chiral pyridoxamines 11 bearing a lateral amine arm. The pyridoxamines exhibited high catalytic activity and excellent enantioselectivity in asymmetric transamination of α-keto acids, to give various α-amino acids in 67–99% yields with 83–94% ee’s. The lateral amine arm likely participates in cooperative catalysis as the Lys residue does in biological transamination and has an important impact on the transamination in terms of activity and enantioselectivity.