Biocatalytic Approaches towards the Synthesis of Chiral Amino Alcohols from Lysine: Cascade Reactions Combining alpha-Keto Acid Oxygenase Hydroxylation with Pyridoxal Phosphate- Dependent Decarboxylation

摘要

Amino alcohols are a very common structural motif in natural and synthetic molecules. Starting from l-lysine and hydroxy-l-lysine, a straightforward biocatalytic synthesis of beta- and gamma-amino alcohols is presented. Diastereoselective C-H oxidation catalyzed by an alpha-keto acid-dependent oxygenase followed by cleavage of the carboxylic acid moiety of the corresponding chiral hydroxy amino acid by a pyridoxal phosphate-dependent decarboxylase enabled the formation of the target amino alcohols with moderate to complete conversions. Four beta- and gamma-amino alcohols were obtained on a small scale in excellent yields and stereoselectivities.