Determination of absolute configurations of amino acids by asymmetric autocatalysis of 2-alkynylpyrimidyl alkanol as a chiral sensor

Asymmetric autocatalysis of 2-alkynyl-5-pyrimidyl alkanol is employed as a chiral sensor of 20 amino acids. Asymmetric autocatalysis using amino acids as chiral initiators gave pyrimidyl alkanols of the absolute configurations that were correlated with those of the amino acids. The enantiomeric excesses of pyrimidyl alkanol are invariably high even when the enantiomeric excess of amino acids is as low as 0.1%. Thus, by determining the absolute configuration of pyrimidyl alkanol with high enantiomeric excess, one can determine the absolute configuration of amino acids even when their enantiomeric excess is low.

Graphical abstractThe absolute configurations of 20 amino acids, even when the enantiomeric excess of amino acid is as low as 0.1%, are determined by asymmetric autocatalysis of 2-alkynyl-5-pyrimidyl alkanol with amplification of enantiomeric excess using as a chiral sensor.Figure optionsDownload full-size imageDownload as PowerPoint slide