Enhancement of whole cell dioxygenase biotransformations of haloarenes by toxic ionic liquids

C. C. R. Allen, C. J. Boudet, C. Hardacre, M. E. Migaud

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Accessing chirally pure cis-diols from arenes using micro-organisms over-expressing toluene dioxygenase (TDO) is now well established, but the conversions remain low for the more toxic and volatile substrates. For such arenes, improved production has already been achieved in the presence of hydrophobic non-toxic ionic liquids (ILs) acting in the form of a reservoir for the arene substrate. Yet, the costs associated with such ILs require extensive process development to render them viable. Herein, we show that optimization of the hydrophobic IL's cationic moiety and of the IL's concentration are key to enhanced conversion yielding between a 2-5 fold yield increase in the conversion of four haloarenes (Ph-X; X = F, Cl, Br, I). Additionally, we report that hydrophilic imidazolium-based ILs offer opportunities to achieve similarly high yielding biotransformations, with further improved reaction rates (<6 h), and this at very low ILs' concentrations (0.0015 VIL/Vaq). We also demonstrate that the increased biotransformations are due to these ILs being inhibitors of cellular respiration processes and thus favoring the shunting of NADH and O2 towards the overexpressed biocatalytic process. © 2014 the Partner Organisations.

    Original languageEnglish
    Pages (from-to)19916-19924
    Number of pages9
    JournalRSC Advances
    Volume4
    Issue number38
    DOIs
    Publication statusPublished - 2014

    Keywords

    • MICROBIAL-CELLS
    • BIOCATALYSIS
    • SYSTEM

    Fingerprint

    Dive into the research topics of 'Enhancement of whole cell dioxygenase biotransformations of haloarenes by toxic ionic liquids'. Together they form a unique fingerprint.

    Cite this