Synfacts 2016; 12(11): 1195
DOI: 10.1055/s-0036-1589424
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Novel Pyridoxamines for Enantioselective Biomimetic Transamination

Benjamin List
Oleg Grossmann
Liu YE, Lu Z, Li B, Tian J, Liu F, Zhao J, Hou C, Li Y, Niu L, Zhao B * Shanghai Normal University, P. R. of China
Enzyme-Inspired Axially Chiral Pyridoxamines Armed with a Cooperative Lateral Amine Chain for Enantioselective Biomimetic Transamination.

J. Am. Chem. Soc. 2016;
138: 10730-10733
Further Information

Publication History

Publication Date:
18 October 2016 (online)



Zhao and co-workers report a novel pyridoxamine catalyst bearing a lateral amine chain. Using this catalyst, they successfully mimicked the transamination activity of transaminases in converting α-keto acids into the corresponding amino acids with commercially available diphenylglycine as the co-substrate; the reaction gave good yields and showed excellent enantioselectivity.



Transamination of α-keto acids is a significant process for generating various amino acids in biological systems; consequently, great efforts have been made since the 1970s to achieve pyridoxamine-based biomimetic asymmetric transamination. In this work, enantioselectivities in excess of 90:10 were achieved under mild conditions for the first time.