Evolving the Promiscuity of Elizabethkingia meningoseptica Oleate Hydratase for the Regio- and Stereoselective Hydration of Oleic Acid Derivatives

Matthias Engleder, Gernot A. Strohmeier, Hansjörg Weber, Georg Steinkellner, Erich Leitner, Monika Müller, Daniel Mink, Martin Schürmann, Karl Gruber, Harald Pichler*

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

The addition of water to non-activated carbon–carbon double bonds catalyzed by fatty acid hydratases (FAHYs) allows for highly regio- and stereoselective oxyfunctionalization of renewable oil feedstock. So far, the applicability of FAHYs has been limited to free fatty acids, mainly owing to the requirement of a carboxylate function for substrate recognition and binding. Herein, we describe for the first time the hydration of oleic acid (OA) derivatives lacking this free carboxylate by the oleate hydratase from Elizabethkingia meningoseptica (OhyA). Molecular docking of OA to the OhyA 3D-structure and a sequence alignment uncovered conserved amino acid residues at the entrance of the substrate channel as target positions for enzyme engineering. Exchange of selected amino acids gave rise to OhyA variants which showed up to an 18-fold improved conversion of OA derivatives, while retaining the excellent regio- and stereoselectivity in the olefin hydration reaction.

Original languageEnglish
Pages (from-to)7480-7484
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number22
DOIs
Publication statusPublished - 27 May 2019

Keywords

  • enzyme catalysis
  • fatty acid hydratase
  • hydrolyases
  • protein engineering
  • substrate promiscuity

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry, Genetics and Molecular Biology(all)

Fields of Expertise

  • Human- & Biotechnology

Treatment code (Nähere Zuordnung)

  • Application
  • Basic - Fundamental (Grundlagenforschung)
  • Experimental

Cooperations

  • BioTechMed-Graz
  • NAWI Graz

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