Synthesis of a precursor of D-fagomine by immobilized fructose-6-phosphate aldolase

PLoS One. 2021 Apr 22;16(4):e0250513. doi: 10.1371/journal.pone.0250513. eCollection 2021.

Abstract

Fructose-6-phosphate aldolase (FSA) is an important enzyme for the C-C bond-forming reactions in organic synthesis. The present work is focused on the synthesis of a precursor of D-fagomine catalyzed by a mutant FSA. The biocatalyst has been immobilized onto several supports: magnetic nanoparticle clusters (mNC), cobalt-chelated agarose (Co-IDA), amino-functionalized agarose (MANA-agarose) and glyoxal-agarose, obtaining a 29.0%, 93.8%, 89.7% and 53.9% of retained activity, respectively. Glyoxal-agarose FSA derivative stood up as the best option for the synthesis of the precursor of D-fagomine due to the high reaction rate, conversion, yield and operational stability achieved. FSA immobilized in glyoxal-agarose could be reused up to 6 reaction cycles reaching a 4-fold improvement in biocatalyst yield compared to the non-immobilized enzyme.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehyde-Lyases / chemistry*
  • Aldehyde-Lyases / metabolism
  • Catalysis
  • Cobalt / chemistry
  • Enzymes, Immobilized / chemistry*
  • Enzymes, Immobilized / metabolism
  • Escherichia coli / enzymology
  • Fructosephosphates / metabolism
  • Imino Pyranoses / chemical synthesis
  • Imino Pyranoses / chemistry*
  • Magnetite Nanoparticles / chemistry*
  • Sepharose / chemistry

Substances

  • Enzymes, Immobilized
  • Fructosephosphates
  • Imino Pyranoses
  • Magnetite Nanoparticles
  • Cobalt
  • fagomine
  • fructose-6-phosphate
  • Sepharose
  • Aldehyde-Lyases
  • fructose-6-phosphate phosphoketolase

Grants and funding

This work was supported by the Spanish MINECO (project No. CTQ2014-53114R), co-financed by European Regional Development Fund. The Department of Chemical, Biological and Environmental Engineering of UAB constitutes the Biochemical Engineering Unit of the Reference Network in Biotechnology, and the research group 2017-SGR-1462, Generalitat de Catalunya. Financial support from Spanish MINECO for the PhD scholarship of Luis Miguel Vázquez and Gerard Masdeu were also received. The authors received also financial support from the Slovenian Research Agency (ARRS) for research core funding No. (P2-0089) and projects No. (J1-7302, J3-7494, and J2-8166).