Novel Pyridoxamines for Enantioselective Biomimetic Transamination
Enzyme-Inspired Axially Chiral Pyridoxamines Armed with a Cooperative Lateral Amine Chain for Enantioselective Biomimetic Transamination.
J. Am. Chem. Soc. 2016;
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.