Highly Efficient Chemoenzymatic Synthesis of l-Phosphinothricin from N-Phenylacetyl-d,l-phosphinothricin by a Robust Immobilized Amidase

J Agric Food Chem. 2020 Dec 9;68(49):14549-14554. doi: 10.1021/acs.jafc.0c06238. Epub 2020 Nov 24.

Abstract

A chemoenzymatic strategy was developed for the highly efficient synthesis of l-phosphinothricin employing a robust immobilized amidase. An enzymatic hydrolysis of 500 mM N-phenylacetyl-d,l-phosphinothricin resulted in 49.9% conversion and 99.9% ee of l-phosphinothricin within 6 h. To further evaluate the bioprocess for l-phosphinothricin production, the biotransformation was performed for 100 batches under a stirred tank reactor with an average productivity of 8.21 g L-1 h-1. Moreover, unreacted N-phenylacetyl-d-phosphinothricin was racemized and subjected to the enzymatic hydrolysis, giving l-phosphinothricin with a 22.3% yield. A total yield of 69.4% was achieved after one recycle of N-phenylacetyl-d-phosphinothricin. Significantly, this chemoenzymatic approach shows great potential in the industrial production of l-phosphinothricin.

Keywords: chemoenzymatic production; enzymatic hydrolysis; immobilized amidase; l-phosphinothricin.

MeSH terms

  • Amidohydrolases / chemistry*
  • Aminobutyrates / chemistry*
  • Bacterial Proteins / chemistry*
  • Biotransformation
  • Enzymes, Immobilized / chemistry
  • Hydrolysis
  • Kinetics

Substances

  • Aminobutyrates
  • Bacterial Proteins
  • Enzymes, Immobilized
  • phosphinothricin
  • Amidohydrolases
  • amidase