A green, fully enzymatic procedure for amine resolution, using a lipase and a penicillin Gacylase

Abstract

A green procedure for the kinetic resolution of chiral amines via enzymatic acylation and deacylation has been demonstrated. The fully enzymatic approach obviates the common, waste-generating deacylation under strongly alkaline conditions. The acylating agent was (R)-phenylglycine propyl ester in combination with Candida antarctica lipase B as acylation catalyst. The enantiomerically enriched amides were subsequently deacylated in the presence of the penicillin G acylase from Alcaligenes faecalis. The degree of enantiomer recognition by CaLB in the acylation of aliphatic amines was unexpectedly modest, but a considerable further enantiomeric enrichment could be accomplished in the course of the subsequent enzymatic hydrolysis step.