Amino acid oxidase‐catalysed resolution and Pictet–Spengler reaction towards chiral and rigid unnatural amino acids

Abstract

BACKGROUND: The biosynthesis of structurally complex isoquinoline alkaloids and other natural products occurs via aromatic amino acids such as tyrosine, and chiral and rigid amino acids. These structures are also key building blocks of many active pharmaceutical ingredients. The aim of this work was the exploration of a rapid and straightforward route to chiral 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid.

Diversity-oriented synthesis of medicinally important 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) derivatives and higher analogs

“…Wohlgemuth and Benz 56 have demonstrated a short coenzymatic two-step route for the synthesis of optically pure Tic derivative 121 from commercially available DL-m-tyrosine 67. In the first step, D-or L-specific amino acid oxidase-catalyzed resolution of DL-m-tyrosine 67 was accomplished.…”

Synthesis of Unnatural/Nonproteinogenic α‐Amino Acids

“…Of course, a racemic mixture of an amino acid can be resolved by the action of an amino acid oxidase in the absence of a chemical reducing agent, but then this is a standard resolution and the maximum yield is 50% and one of the amino acid antipodes is destroyed [172].…”