Achiral amino acid glycine acts as an origin of homochirality in asymmetric autocatalysis

Chiral crystals of the only achiral proteinogenic α-amino acid, glycine induced the asymmetric autocatalysis with amplification of enantiomeric excess (ee). The P 3 1 crystals of γ-glycine, which display positive Cotton effect (CD) at around 215 nm, mediate the asymmetric autocatalysis to yield ( R )-pyrimidyl alkanol with high ee. In contrast, the enantiomorphic P 3 2 crystals, which display negative Cotton effect, afford ( S )-alkanol after the significant amplification of ee by asymmetric autocatalysis. Achiral glycine acts as the origin of chirality in conjunction with asymmetric autocatalysis to afford highly enantioenriched compound.