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

Yong Ethan Liu, Zhaole Lu, Bo Li, Jiaxin Tian, Feng Liu, Junyu Zhao, Chengkang Hou, Yingkun Li, Lili Niu and Baoguo Zhao*

*The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, Shanghai 200234, P. R. China, Email: zhaobg2006hotmail.com

Y. E. Liu, Z. Lu, B. Li, J. Tian, F. Liu, J. Zhao, C. Hou, Y. Li, L. Niu, B. Zhao, J. Am. Chem. Soc., 2016, 138, 10730-10733.

DOI: 10.1021/jacs.6b03930 (free Supporting Information)


Abstract

A class of axially chiral pyridoxamines bearing a lateral amine arm exhibited high catalytic activity and excellent enantioselectivity in asymmetric transamination of α-keto acids, to give various α-amino acids in very good yields and with high ee's. The lateral amine arm likely participates in cooperative catalysis as the Lys residue does in biological transamination and enhances both the activity and the enantioselectivity.


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Key Words

α-amino acids, organocatalysis


ID: J48-Y2016