Hydroxy-amino acids
Hydroxy-amino acids are provided and are prepared by contacting a substituted β-ketodiester having a ketone group and two ester functional groups with a ketoreductase under conditions permitting the reduction of the keytone group to an alcohol. Only one of the ester functional groups is regioselectively hydrolyzed to the corresponding carboxylic acid, whereby a non-hydrolyzed ester functional group remains. The carboxylic acid is converted to an amine to produce a hydroxy-amino acid.
1. A compound having the formula H 2 N—CHR 1 —CH(OH)—(CH 2 ) n —COOH, wherein n is 1 and R 1 is allyl.
2. A compound having the formula H 2 N—CHR 1 —CH(OH)—(CH 2 ) n —COOH, wherein n is 1 and R 1 is propargyl.
3. A compound having the formula H 2 N—CHR 1 —CH(OH)—(CH 2 ) n —COOH, wherein n is 1 and R 1 is 4-pyridyl.
4. A compound having the formula H 2 N—CHR 1 —CH(OH)—(CH 2 ) n —COOH, wherein n is 1 and R 1 is 2-thienyl.
5. A compound having the formula H 2 N—CHR 1 —CH(OH)—(CH 2 ) n —COOH, wherein n is 0 and R 1 is phenyl.
6. A compound having the formula H 2 N—CHR 1 —CH(OH)—(CH 2 ) n —COOH, wherein n is 0 and R 1 is allyl.
7. A compound having the formula H 2 N—CHR 1 —CH(OH)—(CH 2 ) n —COOH, wherein n is 0 and R 1 is propargyl.
8. A compound having the formula H 2 N—CHR 1 —CH(OH)—(CH 2 ) n —COOH, wherein n is 0 and R 1 is 4-pyridyl.
9. A compound having the formula H 2 N—CHR 1 —CH(OH)—(CH 2 ) n —COOH, wherein n is 0 and R 1 is thienyl.