Kinetic resolution of (±)-diethyl- and dibenzyl hydroxy(phenyl)methanephosphonates and their acyl derivatives with lipases

Abstract

A wide variety of commercially available lipases and microbial whole cells were tested for biotransformations of (±)-diethyl and dibenzyl hydroxyl(phenyl)methanephosphonates. Biocatalytic hydrolysis of acylated hydroxyphosphonates by whole cells of Bacillus subtilis gave optically active compounds with 95%ee _S. Enantioselectivities obtained when using commercially available enzymatic preparations were less satisfactory, leading to both compounds with an enantiomeric excess in the range 15 35%. Screening lipases for their ability to acylate these phosphonates or to hydrolyze their acylated derivatives enabled selection of enzymes and organisms suitable for use in both processes.

Keywords::

• kinetic resolution
• hydroxyphosphonates
• microbial hydrolysis
• lipase

Acknowledgement

This work was financed from Project “Biotransformations for pharmaceutical and cosmetics industry” No.POIG.01.03.01-00-158/09-03 part-financed by the European Union within the European Regional Development Fund for the Innovative Economy”.

Declaration of interest: The authors report no declarations of interest.