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- Title
The Substrate Spectrum of the Inverting sec-Alkylsulfatase Pisa1.
- Authors
Schober, Markus; Knaus, Tanja; Toesch, Michael; Macheroux, Peter; Wagner, Ulrike; Faber, Kurt
- Abstract
The substrate spectrum of the inverting alkylsulfatase 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 sulfoxide (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-alcohols via enzymatic hydrolysis of their corresponding sulfate esters, which furnishes homochiral products possessing the 'anti-Kazlauskas' configuration.
- Publication
Advanced Synthesis & Catalysis, 2012, Vol 354, Issue 9, p1737
- ISSN
1615-4150
- Publication type
Academic Journal
- DOI
10.1002/adsc.201100864