title: Biocontrolled formal inversion or retention of L-α-amino acids to enantiopure (R)- or (S)-hydroxyacids.
abstract: Natural L-α-amino acids and L-norleucine were transformed to the corresponding α-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.
authors.affiliation: Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria).
authors.forename: Eduardo
authors.initials: E
authors.lastname: Busto
authors.forename: Nina
authors.initials: N
authors.lastname: Richter
authors.forename: Barbara
authors.initials: B
authors.lastname: Grischek
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Kroutil
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D006880:Hydroxy Acids / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D006880:Hydroxy Acids
keywords: asymmetric catalysis; biocatalysis; cascades; inversion; retention