The substrate spectrum of the inverting sec-alkylsulfatase Pisa1

  • Schober M
  • Knaus T
  • Toesch M
 et al. 
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Abstract

The substrate spectrum of the inverting al- kylsulfatase Pisa1 was investigated using a range of sec-alkyl sulfate esters bearing aromatic, olefinic and acetylenic moieties. Perfect enantioselectivities were obtained for substrates bearing groups of different size adjacent to the sulfate ester moiety. Insufficient selectivities could be doubled by using dimethyl sulf- oxide (DMSO) as co-solvent. Hydrolytically unstable benzylic sulfate esters could be sufficiently stabilised by introduction of electron-withdrawing substituents. Overall, Pisa1 appears to be a very useful inverting alkylsulfatase for the deracemisation of rac-sec-alco- hols via enzymatic hydrolysis of their corresponding sulfate esters, which furnishes homochiral products possessing the ?anti-Kazlauskas? configuration. Keywords:

Author-supplied keywords

  • alkylsulfatase
  • deracemization
  • inversion
  • substrate spectrum

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Authors

  • Peter MacherouxTechnische Universität Graz

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  • Markus Schober

  • Tanja Knaus

  • Michael Toesch

  • Ulrike Wagner

  • Kurt Faber

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