Re-Investigation of Hydration Potential of Rhodococcus Whole-Cell Biocatalysts towards Michael Acceptors

Hanna Busch, Natália Alvarenga, Eman Abdelraheem, Max Hoek, Peter Leon Hagedoorn, Ulf Hanefeld

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Abstract

The implementation of a stereoselective Michael addition with water as substrate is still a major challenge by classical, chemical means. Inspired by nature's ability to carry out this attractive reaction with both high selectivity and efficiency, the interest in hydratases (EC 4.2.1.x) to accomplish a selective water addition is steadily rising. The gram-positive bacterial genus Rhodococcus is known as biocatalytic powerhouse and has been reported to hydrate various Michael acceptors leading to chiral alcohols. This study aimed at the in-depth re-investigation of the hydration potential of Rhodococcus whole-cells towards Michael acceptors. Here, two concurrent effects responsible for the hydration reaction were found: while the majority of substrates was hydrated in an oxygen-independent manner by amino-acid catalysis, an enzyme-catalysed water addition to (E)-4-hydroxy-3-methylbut-2-enoic acid was proven to be oxygen-dependent. 18O2-labelling studies showed that no 18O2 was incorporated in the product. Therefore, a novel O2-dependent hydratase distinct from all characterised hydratases so far was found.

Original languageEnglish
Number of pages7
JournalChemCatChem
Volume11
DOIs
Publication statusPublished - 2019

Keywords

  • alcohols
  • biotransformation
  • hydration
  • labelling studies
  • Rhodococcus

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