Biocontrolled Formal Inversion or Retention of L-α-Amino Acids to Enantiopure (R)- or (S)-Hydroxyacids

Natural L-alpha-amino acids and L-norleucine were transformed to the corresponding alpha-hydroxy acids by formal biocatalytic inversion or retention of absolute configuration. The one-pot transformation was achieved by a concurrent oxidation reduction cascade in aqueous media. A representative panel of enantiopure (R)- and (S)-2-hydroxy acids possessing aliphatic, aromatic and heteroaromatic moieties were isolated in high yield (67-85%) and enantiopure form (>99% ee) without requiring chromatographic purification.