Bioinspired chemical inversion of L-amino acids to D-amino acids

Abstract

An organic receptor (1) that binds a wide variety of amino acids with the same sense of stereoselectivity (D/L ratio of about 10) has been developed. This receptor binds amino acids by formation of imines with internal resonance-assisted hydrogen bonds much as in imines formed between pyridoxal and amino acids. The internal resonance-assisted hydrogen bond is used to activate the bound amino acids and convert L-amino acids to D-amino acids.