Bioinspired Chemical Inversion of l -Amino Acids to d -Amino Acids

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.