Cloning, overexpression, and characterization of a high enantioselective nitrilase from Sphingomonas wittichii RW1 for asymmetric synthesis of (R)-phenylglycine

Appl Biochem Biotechnol. 2014 May;173(2):365-77. doi: 10.1007/s12010-014-0845-y. Epub 2014 Mar 25.

Abstract

In this study, a high (R)-enantioselective nitrilase gene from Sphingomonas wittichii RW1 was cloned and overexpressed in Escherichia coli BL21 (DE3). The recombinant nitrilase was purified to homogeneity with a molecular weight of 40 kDa. The pH and temperature optima were shown to be pH 8.0 and 40 °C, respectively. The purified nitrilase was most active toward succinonitrile, approximately 30-fold higher than that for phenylglycinonitrile. Using the E. coli BL21/ReSWRW1 whole cells as biocatalysts, the kinetic resolution for asymmetric synthesis of (R)-phenylglycine was investigated at pH 6.0. A yield of 46 % was obtained with 95 % enantiomeric excess (ee), which made it a promising biocatalyst for synthesis of (R)-phenylglycine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Aminohydrolases / chemistry
  • Aminohydrolases / genetics*
  • Aminohydrolases / metabolism*
  • Cloning, Molecular
  • Escherichia coli / genetics
  • Escherichia coli / metabolism
  • Glycine / analogs & derivatives*
  • Glycine / biosynthesis
  • Glycine / chemistry
  • Hydrogen-Ion Concentration
  • Kinetics
  • Metals / pharmacology
  • Molecular Sequence Data
  • Recombinant Proteins / chemistry
  • Recombinant Proteins / genetics
  • Recombinant Proteins / metabolism
  • Sequence Alignment
  • Sequence Analysis
  • Sphingomonas / enzymology*
  • Sphingomonas / genetics*
  • Stereoisomerism
  • Substrate Specificity
  • Temperature

Substances

  • Metals
  • Recombinant Proteins
  • 2-phenylglycine
  • Aminohydrolases
  • nitrilase
  • Glycine