One-pot Twostep Chemobiocatalytic Synthesis of a Furan Amino Acid from 5-Hydroxymethylfurfural

Chemistry. 2024 Apr 11;30(21):e202400269. doi: 10.1002/chem.202400269. Epub 2024 Feb 26.

Abstract

Recently, catalytic valorization of biomass-derived furans has received growing interest. 5-Aminomethyl-2-furancarboxylic acid (AMFC), a furan amino acid, holds great promise in the aeras of polymer and pharmaceutical, but its synthesis remains limited. In this work, we report a chemobiocatalytic route toward AMFC by combining laccase-TEMPO system and recombinant Escherichia coli (named E. coli_TAF) harboring ω-transaminase (TA), L-alanine dehydrogenase (L-AlaDH) and formate dehydrogenase (FDH), starting from 5-hydroxymethylfurfural (HMF). In the cascade, HMF is oxidized into 5-formyl-2-furancarboxylic acid (FFCA) by laccase-TEMPO system, and then the resulting intermediate is converted into AMFC by E. coli_TAF via transamination with cheap ammonium formate instead of costly organic amine donors, theoretically generating H2O and CO2 as by-products. The tandem process was run in a one-pot twostep manner, affording AMFC with approximately 81 % yield, together with 10 % 2,5-furandicarboxylic acid (FDCA) as by-product. In addition, the scale-up production of AMFC was demonstrated, with 0.41 g/L h productivity and 8.6 g/L titer. This work may pave the way for green manufacturing of the furan-containing amino acid.

Keywords: amination; biobased chemicals; chemobiocatalysis; furans; oxidation.

MeSH terms

  • Amino Acids
  • Dicarboxylic Acids / chemistry
  • Escherichia coli* / metabolism
  • Furaldehyde / analogs & derivatives*
  • Furaldehyde / chemistry
  • Furaldehyde / metabolism
  • Furans / chemistry
  • Laccase* / chemistry

Substances

  • furan
  • 5-hydroxymethylfurfural
  • Laccase
  • Amino Acids
  • Furans
  • Furaldehyde
  • Dicarboxylic Acids