Production of chiral 1,2-amino alcohols and alpha-amino acids from alkenes by cascade biocatalysis
AssigneeNational University of Singapore
InventorsZhi Li, Shuke Wu
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Abstract
Disclosed herein are methods of forming chiral 1,2-aminoalcohols and α-aminoacids from alkene starting materials by way of an enzymatic cascade reaction sequence that may be accomplished in a single reaction vessel without the need to isolate any intermediates. Also disclosed herein are recombinant nucleic acids, vectors and host cells for use in the methods of the invention.
Claims28
A method for producing an enantiomerically pure or enantiomerically enriched 1,2-amino alcohol or α-amino acid, which method comprises subjecting an alkene starting material to multiple enzyme-catalyzed chemical transformations in a one-pot reaction system, wherein the method comprises generating a vicinal diol from the alkene and an α-hydroxyaldehyde from the vicinal diol.
An isolated nucleic acid molecule encoding at least one heterologous catalytic enzyme selected from the group comprising:
- (a) a dioxygenase for generating a vicinal diol from an alkene by a dihydroxylation reaction, or an epoxidase for conducting an epoxidation reaction to form an epoxide and an epoxide hydrolase for conducting a hydrolysis reaction on the epoxide;
- (b) an alcohol oxidase or alcohol dehydrogenase for generating an α-hydroxyaldehyde or an α-hydroxyketone from the vicinal diol by an oxidation reaction;
- and
- (c) a transaminase or an amine dehydrogenase for generating a 1,2-aminoalcohol from the α-hydroxyaldehyde or the α-hydroxyketone by a transamination reaction or a reductive amination;
- or
- (d) a dioxygenase for generating a vicinal diol from an alkene by a dihydroxylation reaction, or an epoxidase for conducting an epoxidation reaction to form an epoxide and an epoxide hydrolase for conducting a hydrolysis reaction on the epoxide;
- (e) an alcohol oxidase or alcohol dehydrogenase for generating an α-hydroxyaldehyde from the vicinal diol by an oxidation reaction;
- (f) an aldehyde dehydrogenase or an aldehyde oxidase for generating an α-hydroxy acid from the α-hydroxyaldehyde in an oxidation reaction;
- (g) a hydroxy acid dehydrogenase or a hydroxy acid oxidase for generating an α-ketoacid from the α-hydroxy acid in an oxidation reaction;
- and
- (h) a transaminase or an amino acid dehydrogenase for generating an α-amino acid from the α-ketoacid by a transamination reaction or reductive amination reaction.
Dependencies are inferred from the claim text.