Tyramine derivatives catalyze the aldol dimerization of butyraldehyde in the presence of E. coli

Jonathan A. Dennis, Joanna C. Sadler, Stephen Wallace

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

Biogenic amine organocatalysts have transformed the field of synthetic organic chemistry. Yet despite their use in synthesis and to label biomolecules in vitro , amine organocatalysis in vivo has received comparatively little attention – despite the potential of such reactions to be interfaced with living cells and to modify cellular metabolites. Herein we report that biogenic amines derived from L-tyrosine catalyze the self-aldol condensation of butanal to 2-ethylhexenal – a key intermediate in the production of the bulk chemical 2-ethylhexanol – in the presence of living Escherichia coli and outperform many amine organocatalysts currently used in synthetic organic chemistry. Furthermore, we demonstrate that cell lysate from E. coli and the prolific amine overproducer Corynebacterium glutamicum ATCC 13032 catalyze this reaction in vitro , demonstrating the potential for microbial metabolism to be used as a source of organocatalysts for biocompatible reactions in cells.
Original languageEnglish
Article numbere202200238
Number of pages7
Issue number17
Early online date10 Jun 2022
Publication statusPublished - 5 Sept 2022

Keywords / Materials (for Non-textual outputs)

  • biocompatible chemistry
  • bioorganic chemistry
  • organocatalysis
  • whole cells


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