Enzymatic asymmetric synthesis of chiral amino acids

Abstract

Chiral amino acids are extensively applied in the pharmaceutical, food, cosmetic, agricultural, and feedstuff industries. The development of synthetic methodologies for optically pure amino acids has been driven by their significant applications. Among the various synthesis methods for the production of chiral amino acids, enzymatic asymmetric synthesis is a unique preparation strategy that shows great potential. This review provides an overview of the reported methods for enzymatic asymmetric synthesis of chiral amino acids, including asymmetric reductive amination of keto acids, asymmetric transfer of an amino group to keto acids, enantioselective addition of ammonia to α,β-unsaturated acids, and aldol condensation of an amino acid to aldehydes.

Biocatalytic Cascade Reaction for the Asymmetric Synthesis of L‐ and D‐Homoalanine

“…Unnatural amino acids, in high optical purity, attract growing attention for pharmaceutical application as they are useful building blocks for the synthesis of a number of chiral drugs . For instance, L‐homoalanine is a key chiral intermediate in the synthesis of important drugs like antiepileptic (levetiracetam and brivaracetam) and antituberculosis (ethambutol) compounds .…”

“…Unnatural amino acids, in high optical purity, attract growing attention for pharmaceutical application as they are useful building blocks for the synthesis of a number of chiral drugs. [1] For instance, L-homoalanine is a key chiral intermediate in the synthesis of important drugs like antiepileptic (levetiracetam and brivaracetam) and antituberculosis (ethambutol) compounds. [2] The optical purity of these drugs plays an important role in their therapeutic safety and efficacy, where the (R)enantiomer of levetiracetam has no antiepileptic activity and the (2R,2'R) stereoisomer of ethambutol can cause blindness.…”

Broadening the Scope of Biocatalysis in Sustainable Organic Synthesis

“…Fermentation is the method of choice for the industrial synthesis of large‐volume natural l ‐amino acids, such as l ‐glutamate, l ‐lysine, and l ‐phenylalanine. However, the use of isolated enzymes is more attractive for smaller volume l ‐ and d ‐amino acids . Aromatic amino acid lyases catalyze the stereoselective addition of ammonia to cinnamic acids to form α‐amino acids and aminomutases catalyze the 2,3 rearrangement of the amino group and can be used for the enantioselective synthesis of natural and non‐natural α‐ and β‐amino acids…”

Efficient production of phenylpropionic acids by an amino‐group‐transformation biocatalytic cascade

“…Phenylpropionic acids are defined as aromatic carboxylic acids with the C6‐C3 skeleton, mainly including phenylalanines, phenylpyruvic acids, phenylacrylic acids, and phenyllactic acids. They are of great importance in the fields of fine chemicals synthesis, cosmetics, and pharmaceutical manufacturing (Busto et al, ; Busto, Simon, Richter, & Kroutil, ; Hou et al, ; Lütke‐Eversloh, Santos, & Stephanopoulos, ; Xue, Cao, & Zheng, ). For example, tyrosine derivatives play prominent roles in the synthesis of pharmaceuticals (Dennig, Busto, Kroutil, & Faber, ; Seisser et al, ).…”